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Chemistry Carbon
Table of contents
Acetylene, C2H2, ethyne:
Carbohydrates, carbohydrate acids:
Carbohydrate compounds:
Carbon, carbon compounds: 16.4.0
Carbonic acid, soda water: 3.34.3a
Carbolic acid, phenol: 16.1.0
Carboxylic acids:
Fatty acids:

16.1.0 Phenols and Phenolic compounds
16.1.0 Phenol, Carbolic acid
16.1.1 Phenols, phenolics
16.1.2 Phenols, by number of Carbon atoms
16.1.4 Phenolic compounds, by name
16.1.5 Monophenols
16.1.6 Polyphenols

16.2.0 Sugars
Table Aldoses and ketoses
Monosaccharides, D and L sugars:

16.1.0 Phenol, Carbolic acid
See diagram: Phenol
Benzene compounds: See diagram 16.8.1
Coal tar products, creosote: 16.2.10
1 Carbolic acid, C6H5OH, "phenol" from coal tar fraction 170oC to 230oC, colourless hygroscopic crystals.
Phenol is acidic so ionizes in water:
C6H5OH --> H+ + C6H5O-
Do not wash off with alcohol because carcinogenic products or explosive materials may form.
To avoid carcinogenic by-products, use sulfuric acid, not hydrochloric acid, as a catalyst to prepare polymers.
2 "Phenol", carbolic acid (C6H5OH), is a pale pink crystalline solid, solid because of the hydrogen bonds between the phenol molecules.
Pure phenol (carbolic acid) blisters the skin but it is still used in carbolic soaps as an antiseptic.
3 Formerly, it was used as an antiseptic spray in early medical operations.
Other antiseptics and disinfectants include TCP (2.4.6-trichlorophenol), and "Dettol", chloroxylenol (4-chloro-3, 5-dimethylphenol),
(PCMX, para-chloro-meta-xylenol),
4 Phenol as a weak acid: phenol loses a proton, H+ ion, to form a phenoxide ion, C6H5O-.
Phenol reacts with alkalis: phenol + NaOH (aq) <=> sodium phenoxide (aq) C6H5ONa + H2O.
Sodium phenolate, C6H5ONa.3H2O
Halogenation of phenol: phenol + bromine --> 2.4.6-tribromophenol, phenol + chlorine --> 2-chlorophenol, C6H5OHCl
Chlorophenol red, C19H12Cl2O5S, (acid-base indicator): 9.0
Carvacrol, C10H14O
3 TCP, antiseptic for sore throats, was originally trichlorophenylmethyliodosalicyl, but nowadays TCP contains phenol and various phenols.
It has a distinctive "medicine" smell.

16.1.1 Phenols, phenolics
Anthocyanins, anthocyanidins, anthocyanins
Benzfuran, coumarone, C8H6O Chromones
Chromone glycosides
Coumarin, Coumarin, C9H6O2
Coumarone,, C8H6O:
Flavanones, dihydroflavones:
Flavanonols, Taxifolin, C15H12O7, dihydroflavonols:
Flavans, Flavanols:
Isoflavonoids (phytoestrogens):
Lignans, type of polyphenol, in flax, pumpkin seed, sesame, sunflower
Phenol, phenolic, is a derivative of an aromatic hydrocarbon where a hydroxyl group is attached to a benzene ring
Phenolic compounds occur in seeds, grape skins and and are extracted from oak barrels, in citronella, clove oil, dicoumarin, eucalyptol,
ubiquinone, urushiol
Prepare carbol xylol solution: 1.4
Phenol, carbolic acid, TCP, Dettol: 16.1.0
Phenol crystals, C6H5OH, Highly toxic by all routes, lung irritant, corrosive to skin
Phenol solution < 1%, Not hazardous
Phenol-indo-2, 6-dichloro phenol
Phenol fuchsin, carbol fuchsin
Phenols, group: (OH-C).
Phenol, C6H5OH, carbolic acid: 16.1.0
Phenol red, C19H14O5S: 28 (indicator)
Phenolic acids:
Phenolic compounds: 16.1.0
Phenolic ketones, henylacetone, C6Hsub>5CHsub>2COCHsub>3
Quinones, Alizarin, Alkannin, Barbaloin, Juglone. Stilbenoids, resveratrol
Xanthones, gentisin
Miscellaneous phenolics

16.1.2 Phenols, by number of Carbon atoms
C6, Simple phenols: Benzoquinone C6H4O2 (1, 4-benzoquinone)
C7, Phenolic acids,
C8, Tyrosol C8H10O2
C9 Hydroxycinnamic acids,
C10 Napththoquinones,
C15 Emodin, C15H10O5
C6 Quercetin, C15H10O7
C18- Lignans, C18H18O2
C20 Sesamin, C20H18O6
C6- Bioflavonoids, plant polyphenols, phytochemicals:
Arbutin, Asterric acid, Caffeic acid, Caffeoylquinic acid, Coelonin, Coumaric acid, Curcumin,
Dicaffeoylquinic acid, Ferulic acid, Gallic acid, Gastrodin, Honokiol, Hydroxyphenylethanol,
Hydroxytyrosol, Magnolol, Mangostin, Methoxycarnosic acid, Moupinamide, Neochlorogenic
acid from Lonicera japonica, Nirtetralin, Nordihydroguaiaretic acid from Larrea divaricata (creosote bush),
Oleuropein, Osthole, Piceatannol, Plumbagin from Plumbago indica, Resveratrol,
Rosmarinic acid from Rosemarinus officinalis, Shikonin, Shogaol, Silibinin.

Polyphenols are often repeated connected units of:
Catechol, C6H4(OH)2, pyrocatechol, 1, 2-hydroxybenzene
Resorcinol, C6H4(OH)2
Pyrogallol, C6H3(OH)3, 1, 2, 3-trihydroxybenzene
Phloroglucinol, C6H3(OH)3, a phlorotannin.

16.1.4 Phenolic compounds, by name
Anethole, C10H12O
Arbutin, C12H16O7
Bergenin, C14H16O9
Caffeic acid, C9H8O4
Capsaicin, C18H27NO3
Carvacrol, C10H14O
Catechol, C6H4(OH)2
Chlorogenic acid, C16H18O9
Cichoric acid, C22H18O12
Cinnamaldehyde, C9H8O
Cinnamic acid, C9H10O2
Coumaric acid, C9H8O3
Coumarin, C9H6O2
Cresol, C7H8O
Curcumin, C21H20O6
Cyanidin, C15H11O6
Emodin, C15H10O5
Ethylphenol, C8H10O
Estradiol (oestradiol), C18H24O2
Estragole, C10H12O
Eugenol, C10H12O2
Ferulic acid, C10H10O4
Furanocoumarin, C11H6O3
Gallic acid, C7H6O5
Genistein, C15H10O5
Guaiacol, C6H4(OH)(OCH3), Methyoxyphenols:
Juglone, C10H6O3
Mangiferin, C19H18O11
Methyl salicylate, C8H8O3
Myristicin, C11H12O3
Nordihydroguaiaretic acid, C18H22O4
Oleuropein, C25H32O13
Paeonol, C9H10O3
Piceatannol, C14H12O4
Plumbagin, C11H8O3
Quercetin, C15H10O7
Raspberry ketone, C10H12O2
Resorcinol, C6H6O2
Resveratrol, C14H12O3
Rosmarinic acid, C18H16O8
Salicyclic acid, C7H6O3
Sesamol, C7H6O3
Shikonin, C16H16O5
Shogoal, C17H24O3
Silibinin, C25H22O10
Sinapinic acid, C11H12O5
Tannic acid, tea, C76H52O46
Thymol, C10H14O
Tyrosine, C9H11NO3
Tyrosol, C8H10O2
Umbelliferone, C9H6O3
Vanillin, C8H8O3
Zingerone, C11H14O3.

16.1.5 Monophenols, containing one phenolic hydroxyl group
Apiole, parsley, celery leaf
Carnosol, rosemary, mountain deert sage
Carvacrol, oregano, thyme, pepperwort, wild bergamot
Dillapiole, dill weed, fennel root.

16.1.6 Polyphenols Flavonoids (Bioflavonoids), Flavonols, Flavanols Phenolic acids Hydroxybenzoic acids Hydroxycinnamic acids Hydroxyphenylacetic acids Hydroxyphenylpropionic acids Stilbenes Lignans Other polyphenols. Phenylpropanoids Phenolic acids Hydroxybenzoic acids
"hydroxybenzoic acid" may refer to different compounds:
Salicyclic acid, C7H6O3 2-hydroxybenzoic acid
3-hydroxybenzoic acid, C7H6O3, in gut microfauna
4-hydroxybenzoic acid, C7H6O3 --> esters --> parabens
trihydroxybenzoic acid Gallic acid, C7H6O5, hydrolysable tannin, pseudotannin
Benzoic acid, C6H5COOH, C7H6O2
Ellagic acid, C14H6O8. Hydroxycinnamic acids
Caffeic acid, C9H8O4
Chlorogenic acid, C16H18O9
Cichoric acid, C22H18O12
Cinnamic acid, C9H10O2
Coumaric acid, C9H8O3
Ferulic acid, C10H10O4
Rosmarinic acid, C18H16O8
Sinapinic acid, C11H12O5. Hydroxyphenylacetic acids - Polyphenols
Methoxyphenylacetic acid, C9H10O3. Hydroxyphenylpropionic acids - Polyphenols
Dihydrocaffeic acid, C9H10O4. Stilbenes - Polyphenols
Pallidol, C28H22O6
Piceatannol, C14H12O4
Resveratrol, C14H12O3. Lignans - Polyphenols
Lignans: (from degradation of lignin), plant phenols, dihydroguaiaretic acid, hinokinin, podophyllotaxin
Honokiol, C18H18O2, neilignan biphenol, spicy odour, in traditional Asian herbal medicine, analgesic, treat anxiety
Magnolol, C18H18O2, in traditional herbal medicine, antifungal, in bark of Magnolia grandiflora, M officinalis
4-O-methylhonokiol, C19H20O2, in bark of Magnolia grandiflora
Sesamin, C20H18O6, in sesame oil, Sesamum indicum, and in bark of Fagara cujabensis
Sesame oil, Composition of edible oils: 19.2.11 (Table)
Sesamol, C7H6O3
Aviculin, C26H34O10, in Knotgrass
Pinoresinol, C20H22O6
Matairesinol, C20H22O6
Todolactol A, C20H24O7
Trachelogenin, C21H24O7. Other polyphenols - Polyphenols
Arbutin, C12H16O7
Catechol, C6H4(OH)2, C6H6O2
Phenol, C6H6O, Carbolic acid: 16.1.0
Phlorin, C12H16O8
Pyrogallol, C6H3(OH)3, 1, 2, 3-trihydroxybenzene, C6H6O3. Alkylmethoxyphenols
4-Ethylguaiacol, C9H12O2
4-Vinylguaiacol, C9H10O2
4-Vinylsyringol, C15H14O3. Alkylphenols
4-Ethylcatechol, C8H10O2
4-Ethylphenol, C8H10O. Curcuminoids
Curcumin, C21H20O6
Demethoxycurcumin, C20H18O5. Furanocoumarins
Bergapten, C12H8O4
Psoralen, C11H6O3. Hydroxybenzaldehydes
Gallic aldehyde, C7H6O4
Vanillin C8H8O3. Hydroxybenzoketones
3-Methoxyacetophenone, C9H10O2. Hydroxycinnamaldehydes
Ferulaldehyde, C10H10O3
Sinapaldehyde, C11H12O4. Hydroxycoumarins
Coumarin, C9H6O2
Esculetin, C9H6O4
Esculin, C15H16O9. Hydroxyphenylpropenes
Anethole, C10H12O, monoterpene
Estragole, C10H12O, methyl chavicol
Eugenol, C10H12O2
Gingerol, C17H32O4. Methoxyphenols
Guaiacol C6H4(OH)(OCH3), C7H8O2. Napththoquinones
Naphthoquinones, C6-C4 skeleton
1, 2-Naphthoquinone, C10H6O2, in diesel exhaust.

1, 4-Naphthoquinone, C10H6O2, strong odour, red-brown alkaline solution, cytotoxic derivatives in vitamin K
Triphophyllum peltatum
Napthoquinone derivatives
Drosera species
Droserone, C11H8O4
Plumbagin, C11H8O3
Juglone, C10H6O3
Alkannin, C16H16O5. Phenolic terpenes
Carnosol, C20H26O4
Carvacrol, C10H14O
Thymol, C10H14O, monoterpene. Tyrosols
Oleuropein, C25H32O13
Tyrosol, C8H10O2. Phenylpropanoids
aromatic ring + attached three-carbon chain
Anethole, C10H12O
Apiole, C12H14O4
Caffeic acid, C9H8O4
Chlorogenic acid, C16H18O9
Cichoric acid, C22H18O12
p-Coumaric acid, C9H8O3
Curcumin, C21H20O6
Estragole, C10H12O
Eugenol, C10H12O2
Ferulic acid, C10H10O4
Myristicin, C11H12O3
Rosmarinic acid, C18H16O8
Safrole, C10H10O2
Sinapic acid, C11H12O5 Acetylene Acetylene, C2H2, ethyne Prepare acetylene Tests for acetylene Oxyacetylene welding Tests for gases from burning hydrocarbons. Acetylene
Acetylene, C2H2, ethyne, Use acetylene in a fume cupboard or use very small quantities in a well-ventilated area.
Use eye and skin protection to avoid splashes.
Mixtures of acetylene and air may be dangerously explosive.
Also, explosive acetylides form when acetylene reacts with silver or copper (I) salts.
Formerly, bicycle "carbide lamps" used calcium carbide + water --> acetylene + calcium hydroxide.
However, the calcium carbide used to decompose in moist air to form the unpleasant odour of acetylene.
The gas has a foul smell because of the presence of traces of phosphorus hydrides.
This decomposition could be lessened by pouring petroleum over the calcium carbide to exclude air and moisture.
Acetylene forms highly explosive mixtures with air, but is otherwise not toxic.
As prepared from the reaction of calcium carbide with water, it usually has an evil smell because of the presence
of small amounts of phoshpines, R3P.
Do not inhale the impure gas.
Handle acetylene cylinders with care.
Unplanned release of a large quantity of acetylene may result in a serious fire or explosion.
In acetylene cylinders, acetylene is dissolved in acetone supported on a porous diatomaceous earth base.
The pressure inside an acetylene cylinder is therefore lower than in other cylinders that contain compressed gases, e.g nitrogen. Prepare acetylene
See diagram 16.1.5: Prepare ethyne
The main hazard with calcium carbide is the ignition of air / acetylene mixtures.
A violent explosion may occur, depending on the proportions of air and acetylene.
Acetylene, when undiluted with air, burns with a smoky flame.
Before igniting acetylene, be sure that it is not mixed with air.
Purchased calcium carbide usually contains sulfur and phosphorus compounds that react with water to form strongly smelling
gaseous impurities that act as a convenient indicator for the presence of acetylene.
1 In a fume cupboard, put a 2 g lump of calcium carbide in a 250 mL beaker.
Add water drop-by-drop.
Calcium carbide reacts vigorously with water forming acetylene gas (ethyne) and releasing a considerable amount of heat.
Ignite the resulting bubbles of acetylene.
2 On a metal tray or shallow container in a fume cupboard, add water drop-by-drop to one lump of calcium carbide.
The water will hiss and the gas will be produced.
The lump will fall to pieces to form a powder of calcium hydroxide.
Do not attempt to ignite the acetylene produced.
3 Put a < 5 g lump of solid calcium carbide in 500 mL of water and ignite the ethyne produced.
Do this experiment outside, with the observers at least 2 metres away.
4 Formerly, bicycle "carbide lamps" used the following reaction.
Put sand in a dry test-tube and add pieces or lumps (not powder) of calcium dicarbide (calcium carbide).
Add water drop by drop.
Collect the gas over water.
CaC2 + 2H2O -> C2H2 + Ca(OH)2
calcium dicarbide + water -> ethyne (acetylene) + calcium hydroxide
5 Collect acetylene from oxy-acetylene equipment. Tests for acetylene
Light the gas in the test-tube with a glowing splint.
The gas burns with a smoky flame. Tannins, plant polyphenols
1 Hydrolyzable tannins
Ellagitannins, C44H32O27, e.g. emblicanin A, emblicanin B, punigluconin, pedunculagin
See diagram Ellagitannin
Gallic acid, C7H6O5, hydrolysable tannin, pseudotannin

2 Condensed tannins Flavones, condensed tannins, non-hydrolysable tannins, Anthoxanthins

3 Phlorotannins
Phloroglucinol, C6H3(OH)3, a phlorotannin.

Tannins are polyphenolic compounds with large molecular weights that have enough hydroxyl groups for effective cross linking with
other compounds, astringents.
Tannins are usually divided into hydrolyzable tannins and condensed tannins.
However, the term "tannins" has been applied to any compound or plant extract that could make skin collagen impervious to degradation,
i.e make leather.
Tannins are any group of yellow-brown astringent compounds derived from gallic acid, found in bark and galls, used to convert animal
hide to leather.
The word "tannin" is based on the Celtic word for oak tree.
Tannins from hemlock (Tsuga), oak (Quercus), mangrove, (Rhizophora), wattle (Acacia), babul (Acacia sp) chestnut (Castanea),
quebracho (Schinopsis), sumacs (Rhus), canaigre from tanner's dock (Rumex).
Tannin, i.e tannic acid, a polyphenol, is a yellow brown compound in coffee beans, oak galls, mahogany, tea leaves, tree bark, walnuts.
Reacts with proteins in skins to form leather.
Used as a mordant, inks and dyeing.
E181 Tannic acid, is not an acid, but is usually shown as C75H52O46, decagallol glucose, but is probably a more complex mixture of
glucoses and esters.
Tannic acid (a polyphenol), in Caesalpinia, Rhus, does not occur in green tea or black tea
Tannic acid is a light yellow to tan solid with a faint odour which sinks and mixes with water.
Tannic acid and tea
Tannic acid is present in oak galls.
Make a solution of tannic acid by boiling cut pieces of oak galls in water.
Tannic acid is sold as a brown powder and was used in tannic acid jelly for burns dressings.
Tea from Camellia sinensis, has a slightly bitter, astringent flavour.
Tea contains polyphenols, but tea does not contain tannic acid as previously believed.
Tannic acid is a dyeing mordant, slightly toxic if ingested.
Use tea solution to polish linoleum, windows and mirrors, remove fish smell and shine from seats of skirts or blue serge suits,
deodorizes feet, dye greying white fabrics, highlight brown hair, treat sunburn pain, with lemon treat sore throat, diarrhoea, sore eyes,
burns, bleeding gums, broken finger nail, speed grass seed germination and house plant growth, with lemon deodorize stuffy rooms,
clean and polish black lacquer and varnished woodwork, tenderize meat.
List of tannins: Flavonols, flavan-3-ols, catechins
Catechin, Catechin hydrate, Catechin gallate from green tea
Chebulinic acid
Ellagic acid: from tree bark
Epicatechin from green tea, Epicatechin gallate from green tea
Epigallocatechin: from green tea
Epigallocatechin gallate
Gallocatechin, Gallocatechin gallate from green tea,
Punicalagin from pomegranate, Trigalloylglucose Carbohydrates, carbohydrate acids
Burn carbohydrates, fats and proteins: 16.9.1
Tests for carbonates:
Tests for carbohydrates, Molisch's test: 9.134
Carbohydrate acids:
D-gluconic acid, CH2(OH)(CHOH)4COOH, produced by fungi
D-glucuronic acid, C6H10O7, in gums, forms glucuronides
d-gluconic acid, d-glucuronic acid, food additive E574, anti-caking agent, sequestrant
Sold as: D-Glucuronic acid, Glucodiuronic acid, C6H10O7. Carbohydrate compounds
Carbohydrates were compounds such as aldoses and ketoses, stoichiometric formula Cn(H2O)n, so "hydrates of carbon".
Nowadays, carbohydrates include monosaccharides, oligosaccharides and polysaccharides, and substances from monosaccharides,
1 by reduction of the carbonyl group, >C=O (alditols),
Carbonyl, >C=O, organic compound functional group
2 by oxidation of one or more terminal groups to carboxylic acids, e.g ethanoic acid, CH3COOH,
3 by replacement of hydroxy groups by a hydrogen atom, amino group, thiol group, other groups, derivatives of these compounds. Sugars
9.142 Fehling's test
See diagram Glucose and fructose, straight chain forms
Sugars are simple carbohydrates, one or more monosaccharide units, soluble in water, optically active, sweet to taste and fermentable.
However, the term "sugar" generally refers to monosaccharides and lower oligosaccharides.
"Reducing sugars" reduce copper (II) to copper (I) salts in Fehling's solution or other test solutions, show presence of aldehyde group.
Monosaccharides have a straight chain form or ring form, cannot be split into smaller molecules using dilute acids, cannot be hydrolysed
to simpler compounds.
Polysaccharides have more than ten monosaccharides linked by glycosidic bonds, between C1 on one sugar and C4 on other sugar by
removal of water molecule, i.e a condensation reaction.
An aldose has aldehyde group, -CHO, i.e a carbonyl, group, C=O, with a hydrogen atom attached to the carbon atom, e.g glucose. Monosaccharides
| Apiose | Arabinose | Deoxyribose | Digitalose | Fructose | Galactose | Galacturonicacid | Glucosamine | Glucose | Glucuronic acid |
| Hamamelose | Mannose | Rhamnose | Ribose | Ribulose | Sorbose | Xylose |
| See diagram Aldose: D-glyceraldehyde, L-glyceraldehyde, Ketose: dihydroxyacetone
| See diagram Aldose sugar: Glucose
| See diagram Aldose sugar: Galactose
| See diagram Ketose sugar: Fructose
| See diagram Aldose sugar: Ribose, deoxyribose, nucleotide
Monosaccharides, Cx(H2O)y, where x = 1 or 2 or 3, contain a single sugar unit, e.g glucose, fructose.
So they cannot be hydrolysed to simpler sugars.

Classification: of monosaccharides
1 Classification by number of carbon atoms
Triose, 3 carbon atoms, C3H6O3, dihydroxyacetone, glyceraldehyde
Tetrose, 4 carbon atoms, C4H8O4, e.g. erythrose, threose, erythrulose
Pentose, 5 carbon atoms, C5H10O5, e.g. arabinose, lyxose, ribose, xylulose
Hexose, 6 carbon atoms, C6H12O6, e.g. allose, altrose, glucose, mannose, gulose, idose, galactose, talose.

2 Classification by whether aldose or ketose
An aldose contains the aldehyde group (-CHO), at C1, monosaccharide bonded to an aldehyde chain, Cn(H2O)n, e.g glyceraldehyde,
(CHOCHOHCH2OH), the simplest aldose
An aldose sugar is also an aldehyde which contains one aldehyde group per molecule.
A ketose contains the ketone group (-CO-), at C2, monosaccharide sugar containing a ketone group or compound derived from a ketone,
e.g dihydroxyacetone (CH2OHCOCH2OH), the simplest ketose
A ketone group is a carbonyl group, C=O, with two single bonds to other carbon atoms.
A ketose sugar contains one ketone group per molecule, e.g fructose, CH2OHCHOHCHOHCHOHC=OCH2OH
Ketose sugars include Glycerone, C3H6O3, dihydroxyacetone, simplest ketose sugar, triose, stains skin brown but no increase in melanin so used in
sunless tanning, fake sun tan.
Sold as: Dihydroxyacetone, 1, 3-Dihydroxy-2-propanone, DHA, Glycerone
Xyulose, C5H10O5, pentose, not used as commercial sweetener
Sold as: D-Xylulose, D-threo-Pentulose, faint yellow syrup.
Table Aldoses and ketoses
C Atoms
Aldose sugars contain an aldehyde group, R-(CHO)
Ketose sugars contain a ketone group, R1R2>(C=O)
3 C triose
Glyceraldehyde |
Dihydroxyacetone |
4 C tetrose
Erythrose | Threose |
Erythrulose |
5 C pentose
Arabinose | Ribose | Xylose | Ribulose |
6 C hexose
Galactose | Glucose |Mannose | Fructose | Sorbose |

D-Apiose, C5H10O5 monosaccharide, in parsley, (Petroselenum crispum) as the flavone glucoside Appiin,
in polysaccharides of aquatic plants,
in Lemna, Posidonia, Wolffia, Zostera.

L-Arabinose, C5H10O5, pectinose, pectin sugar, in plant glycosides, hemicelluloses and gums
Sugar component of anthroquinone glycosides of Aloe.
Arabinose, (Table)
Arabinose is sold as L-(+)-Arabinose

2-Deoxy-D-ribose, Desoxyribose, C5H10O4
Sugar component of desoxyribonucleic acid, DNA, prepared by acid hydrolysis of DNA Nucleosides, nucleic acids, DNA, RNA
4.4.0H DNA and RNA.

C7H14O5, in cardiac glycosides, in common foxglove (Digitalis purpurea).

See diagram: Fructose
C6H12O6, Fructose, D form, but laevorotatory, so "L-fructose", sold as: "D-(-)-Fructose, D-Levulose, Fruit sugar", pure honey
Fructose, (Table)
Occurs as free sugar in phloem and nectar, in oligosaccharides, e.g. sucrose, twice as sweet as glucose
Tests for glucose and fructose with Fehling's solution: 9.142.4.
Tests for reducing sugars gives no values for fructose.

Galactose, C6H12O6, L-Galactose, Brain sugar, Cerebrose, sold as: D-(+)-Galactose
Galactose, (Table)
In hemicelluloses of pectins, gums, mucilages, in some glycosides, sugar of seaweed polysaccharides, Porphyra
Lactose, milk sugar = (glucose + galactose), lactase decomposes lactose molecules to α-glucose and β-galactose.
Repeating disaccharide unit, "poly β-galactose--β-acetylglucosamine-6-sulfate", in bovine cornea.
Bacteroides thetaiotaomicron in the colon harvests additional energy from otherwise indigestible sugars, e.g. galactose and mannose.
Tests for reducing sugars gives no values for galactose.
Caramelization temperature of galactose is 160oC.

Galacturonic acid
C6H10O7, in polymers in plant cell wall pectin, in saponins, Marchantia moss.

C6H13NO5, 2-amino-2-deoxyglucose, sugar in animal chitin and mucoprotein
monosaccharide amino sugar, from fermentation of grain, anti-arthritic and may help relieve symptoms of arthritis, but
scientific evidence is not conclusive and it may interact with warfarin, so large doses are not advised.
Glucosamine dietary supplements should be taken with food to avoid upset stomach, heartburn and diarrhoea
In bacteria and fungi cell wall, Aspergillus, in glycoproteins of plant seeds, Phaseolus.

Glucuronic acid
C6H10O7, in plant gums and mucilage, in Miquel's Wintergreen Gaultheria miqueliana.

C6H12O6, with tannin in bark of witch hazel (Hamamelis virginiana), in leaves of Primula.

C6H12O6, in plant polysaccharides, in natangura palm (Metroxylon warburgii)
. Mannose (Table)
Mannitol CH2OH(CHOH)4CH2OH, from mannose or fructose, sugar in fungi and brown algae, food sweetener.
Sold as D-Mannitol, Mannite, C6H14O6.
Early purple orchid (Salep dondurma), fox testicle, ground tuber in turkish ice cream "dondurma" (glucomannams: glucose +mannose).
Sold as: D-(+)-Mannose from wood, D-Mannopyranose, L-(-)-Mannose.

C6H12O5, deoxy sugar in many plant glycosides and polysaccharides, especially pectins, gums, very sweet taste.
Quercitrin, C21H20O11, Fagopyrum, (Quercus --> Quercetin and Rhamnose)
Quercitrin, in allspice herb, a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose, is in the dye quercitron.
Deoxy sugar rhamnose in alder buckthorn (Rhamnus frangula), frangula bark, a former laxative.

C5H10O5, D-ribose, in ribonucleic acids, and metabolic ATP, adenosine
Ribose, (Table)
See diagram Ribose, deoxyribose
Ribose has all the hydroxyl groups on the same side in the Fischer projection.
Industrial: D-(-)-Ribose, 099%, CAS Number 50-69-1, Empirical Formula C5H10O5, Molecular weight 150.13
Adenosine, C10H13N5O4 (adenine + ribose), adenine riboside, adenine-9-β-D-ribofuranoside
Deoxyribose, DNA and RNA: 4.4.0
Guanosine, C10H13N5O5, nucleoside, (guanine + D-ribose)
Roasting meat:

C5H10O5, D-Riboketose, arabinoketose, in photosynthesis carbon cycle, sweet tasting
Ribulose, (Table)
See diagram D-ribulose and L-ribulose
Ribulose is a ketopentose so has a ketone functional group.
It is an artificial sweetener, but not very sweet.
The enantiomers (mirror image molecules, pair of optical isomers), are D-ribulose and L-ribulose.
Ribulose-5-phosphate-3-epimerase, catalyses L-ribulose 5-phosphate <==> L-xylulose 5-phosphate
RuBisCO, carbon fixing enzyme, ribulose-1, 5-bisphosphate carboxylase, start of photosynthesis enzyme.
RuBisCO, C5H12O11P2, ribulose-1-5 biphosphate carboxylase oxygenase, the most abundant enzyme for first step in carbon fixation by plants.
Sold as: RuBisCO, powder from spinach
Ribulose is sold as: L-Ribulose, L-Adonose, also D-Ribulose

C6H12O6, in pectins of ripe passionfruit, (Passiflora edulis), in fruit of mountain ash (Sorbus aucuparia), in ascorbic acid metabolism cycle
Sorbose, (Table).

C5H10O5, D-Xylose, wood sugar, in mist plant glycosies or polysaccharides called xylans, very sweet taste
Arabinoxylans in cell walls, wood, and cereal grains is a combination of arabinose and xylose.
In Psyllium (Plantago ovata)
Xylose, (Table).

2 to 6 monosaccharide units, only sucrose in all plants, Raffinose and Stachyose in most legume seeds

C36H62O31, hexasaccharide, sweet, in Ajuga, verbascum, seeds of Vicia, Vigna mungo

C18H32O16,sweet, trisaccharide, plant metabolite, reserve carbohydrate, in Gentiana rhizomes

C12H22O11, bitter, two beta-D-glucose residues linked, in plant glycosides, e.g. amygdalin

Lactose, experiments
C12H22O11, glycosylglucose disaccharide, glucose galactoside, milk sugar, not as sweet as sucrose, nutrient for infants and convalescents,
in Forsythia flowers, Achras fruit
Lactose, milk sugar = (glucose + galactose), lactase decomposes lactose molecules to α-glucose and β-galactose.

C12H22O11, sweet, in Colchicum petals, some plant glycosides, made from seaweed polysaccharide laminarin
antiseptic, formed from caramelization of glucose

C12H17O10Na, sweet, in cress, sunflower and buckwheat seeds, Lepidium

C24H42O21, tetrasaccharide, reserve carbohydrate, sweet, in Lychnis, Dianthus, woody plants, cucurbits and legumes.

C12H22O11, malt sugar, maltobiose, disaccharide of two glucose molecules with α(1→4) glycosidic linkage, from starch in food and
action of amylase, in beer, cereals, pasta, less sweet than cane sugar, some maltose in many plants especially pollen and nectar, used in
brewing, soft drinks, food products nutients for invalides.

C18H32O16,sweet, nonreducing trisaccharide sugar, in pine manna, Pinus, Pseudotsuga, aphids Cinara honeydew attracts ants, bees.

C18H32O16,gossypose, melitose, trisaccharide, in plant leaves, Vicia, sugar beet Saccharomyces cerevisiae , cotton seed, reserve carbohydrate.

C24H42O21, sweet, in sesame Sesamum, reserve carbohydrate.
Sesame oil, Composition of edible oils: 19.2.11 (Table)

C24H42O21, sweet, in Stachys roots, Jasminum, Lupinus, Fraxinus.

C12H22O11, sweet, disaccharide formed by glucose and fructose units, in green plants especially nectars, sugar cane preservative,
Saccharomyces cerevisiae metabolite.

C12H22O11, disaccharide, mycose, mushroom sugar, sweet, in fungi, some prevent desiccation function.

C18H32O16,trisaccharide, sweet, in Angelica, Aegopodium, reserve carbohydrate.

C30H52O26,pentasaccharide (stachiose + alpha-D-galactopyranose), sweet, in green plants storage organs, Verbascum. Carboxylic acids
Carboxylic acids (fatty acids), R-(COOH)n, contain the carboxyl group -CO.OH, i.e -COOH, carbonyl group attached to an
hydroxyl group, are weak acids, e.g ethanoic acid (acetic acid) CH3COOH, so the general formula is RCOOH.
An anion formed from carboxylic acid is called a carboxylate.
The carbonyl group (carboxy) is -COOH. Fatty acids
The group of saturated and unsaturated aliphatic carboxylic acids are called fatty acids and are found as esters in fats and oils.
Lower carbon fatty acids are corrosive liquids with strong odour and are soluble in water.
Higher carbon fatty acids are oily liquids with unpleasant smell and are only slightly soluble in water.
Fatty acids from C10 onwards are usually solids and are insoluble in water.
The poly unsaturated fatty acids linoleic acid, linolenic acid and arachidonic acids are essential fatty acids in the diet to prevent
atheroma ("hardening of the arteries"), and synthesize prostaglandins.
Saturate fatty acids with no double bonds are linked to the development of atheroma.
Fatty acids in plants occur as esters of glycerol or other hydroxy compound, or amides of long chain amines, e.g sphingenine.
Fatty acids have trivial and systemic names and the molecule may be saturated (no double bonds), or unsaturated (one or more
double bonds).
The products called "natural oils" are not necessarily unsaturated fats.

List of fatty acids
Arachidic acid, C20H40O2, in seed oils, Peanut (Arachis hypogaea)
Arachidonic acid, C20H32O2, only in algae, mosses and ferns
Behenic acid, C22H44O2, in Rocket
Chaulmoorgric acid, C18H32O2, in Chaulmoogra (Hydnocarpus wightiana)
Decanoic acid, C20H40O2, in Chilli (Capsicum species)
Erucic acid, C20H40O2, in Nasturtium (Tropaeolum majus)
Hexanoic acid, C20H40O2, in Devil's trumpet (Datura metel), in Coconut (Cocos nucifera)
Lauric acid, C20H40O2, in Coconut (Cocos nucifera)
Linoleic acid, C20H40O2, in Borage (Borago officinalis)
Linolenic acid, C20H40O2, in Perilla (Perilla frutescens var. crispa)
Myristic acid, C20H40O2, in Orris (Iris florentina)
Oleic acid, C20H40O2, in Chinese date (Zizyphus jujuba)
Palmitic acid, C20H40O2, in Abelmosk (Abelmoschus moschatus)
Palmitoleic acid, C20H40O2, in Coconut (Cocos nucifera)
Petroselenic acid, C20H40O2, in Parsley (Petroselinum crispum)
Ricinoleic acid, C20H40O2, in Golden shower tree (Cassia fistula)
Stearic acid, C20H40O2, in Coconut (Cocos nucifera)
Vaccenic acid, C20H40O2, in Milkweed (Asclepias syriaca)

Catechol, C6H4(OH)2, [C6], simple phenol, 1, 2-dihydroxybenzene, colourless crystalline phenol, harmful, irritant, pyrocatechol,
powder, Catechol, benzene-1, 2-diol, C6H6O2.

Cichoric acid, C22H18O12, an hydroxycinnamic acid, in Chicory, dandelion leaves, basil, lemon basil.

Coumaric acid, C9H8O3, p-Coumaric acid, a hydrocinnamic acid, in Gnetum.

Ethylphenol, C8H10O, 2-Ethylphenol, C2H5C6H4OH, 4-Ethylphenol, 4-Ep, from fungus, spoils taste in wine and beer.

Eudesmol, C15H26O, alpha- and beta-eudesmol, beta-selineneol, woody odour, sesquiterpenoid alcohol, in Atractylodes lancea,
neuromuscular block.

Ferulic acid, C10H10O4, [C6-C3], an hydroxycinnamic acid, trans-Ferulic acid, caffeic acid 3-methyl ether, common because in pectin
and lignin, accumulates in leaves of Beta vulgaris, beetroot.

Oleuropein, C25H32O13, (a phenyl ethanoid phenolic compound), in Olive oil, anti-inflammatory, antioxidant, anti-thrombotic, anti-athergenic.

Piceatannol, C14H12O4, (a stilbenoid phenolic compound), anti-leukemia, in root of Picea abies | Gnetum cleistostachyum, |
Aiphanes horrida | Stilbenoid glucoside, C20H22O8, piceid.

Paeonol, C9H10O3, antimutagenic, analgesic, portects liver, anti-inflammatory, in mountain peony
Japanese mountain yam.

Raspberry ketone, C10H12O2, used in perfumes, as food additive, synthetic much cheaper than natural product, in Raspberry |

Rosmarinic acid, C18H16O8, antioxidant, anti-inflammatory, antimicrobial, in Rosemarinus officinalis, Maranta bicolor.

Sesamol, C7H6O3, white crystalline solid, in sesame seeds, sesame oil, antioxidant, prevents oil spoilage.

Shikonin, C16H16O5, naphthaquinone, anti-inflammatory, traditional chinese medicine, zicao, anti-cancer, in Arnebia, Lithospermum erythrorhizon.

Silibinin, C25H22O10, in Silymarin, anticancer.

Sinapic acid, C11H12O5, widespread, in peel of Citrus limon, antibacterial, antifungal

Sinapinic acid, C11H12O5, an hydroxycinnamic acid, a phenylpropanoid, sinapine, in black mustard seed.

Tyrosol, C8H10O2, [C6-C2]
Tyrosol is an antioxidant phenolic compound, in red and white wines, olive oil, vermouth and beer.

Urushiol, mixture of catechol molecules substituted with different alkyl chains, in poison ivy, used in lacquer ware, causes allergic
reactions in people handling mango leaves and stems.

Vanillin, C8H8O3, phenolic aldehyde, vanilla aroma.

16.4.0 Carbon, carbon compounds
Carbon (Commercial)
Carbon, C, Organic chemistry: 16.1.0
Carbon C, Table of Elements
Carbon properties: 16.4.1
Carbon chemical reactions: 16.1.0
Carbon / nitrogen ratio: 9.14.3, (Composting, agriculture)
Carbon atom, Size of carbon atom size in stearic acid molecule:
Carbon, Activated carbon for decoloration application, activated charcoal (commercial product): 11.0
Carbon, Allotropes, sulfur, carbon:
Carbon, "Aquadag": 35.41.5
Carbon, Burn to make carbon (Primary): 5.43
Carbon, charcoal blocks, 35.41.1
Carbon atom size in a stearic acid molecule:
Carbon, charcoal blocks, 35.41.1
Carbon chemical reactions, Organic chemicals: 16.1.0
Carbon dioxide, CO2: 3.34
Carbon disulfide, CS2: 16.4.4
Carbon monoxide, C≡O (note triple bond): 16.4.5
Carbon tetrabromide, CBr4
Carbon tetrachloride, CCl4, Tetrachloromethane.

Carbonated beverages, Soft drinks, fizzy drinks, sports drinks: 15.8.6
Carbonated water, club soda, soda water: 3.34.3
Carbonated water, Freezing point, cola: 24.1.05
Carbonic acid, carbonated water, H2CO3, soda water: 3.34.3a
Carbonyl, >C=O, organic compound functional group
Coal, airborne coal dust explosions: 35.23.1 (Geology)
Coal seam gas, CSG, and coal to liquid, CTL, projects: 35.23.9
Concentrated acids with a non-metal, carbon: 12.3.14
Dilute acids with non-metals, carbon, sulfur: 12.3.4
Graphite, "lead pencil", "Aquadag", C: 35.41.3
Graphite, Allotropes, sulfur, carbon:
Heat glucose to form carbon: 12.7.1
Jet black
Radioactive carbon dating: 2.10.1
Separate by melting points, tin from tin and carbon mixture: 3.18
Slate (C + clay, mudstone, shales): 35.23.6 (Rock)
Soot from a candle flame, carbon: 8.1.2a
"Lead pencil": 35.41.4
Heat glucose to form carbon: 12.7.1
Organic carbon soil test: 6.50.9
Prepare gases from wood: 3.99
Radioactive carbon dating: 2.10.1
Separate by melting points, tin from tin and carbon mixture: 3.18
Slate (C + clay, mudstone, shales): 35.23.6 (Rock)
Soot from a candle flame, carbon: 8.1.2a.

16.4.1 Carbon, properties
Carbon, C (Latin carbon coal), lump, rods, powder, lamp black, acetylene black, wood charcoal, activated carbon / charcoal,
activated charcoal, decolorizing charcoal, graphite, colloidal carbon, carbon mineral lump (coke is left when coal is heated without air,
for blowpipe work, charcoal may contain wood ash mainly potassium carbonate, soft "lead" pencils), non-metal network solid, has two
natural crystalline forms, diamond and graphite.
Atomic number: 6, Relative atomic mass: 12.011, r.d 2.25 (graphite), mp: 3730oC (sublimes), bp: 4830oC,
Specific heat capacity 711 J kg-1 K-1 (graphite), 519 J kg-1K-1 (diamond)
Carbon, black central electrode of torch (flashlight) batteries
Carbon nanotubes, Activated carbon, Darco KB and KB-B activated carbon, for purifying highly coloured liquids.
Low cost: activated charcoal from pharmacies and stores selling pet fish, goldfish and aquariums.

16.4.4 Carbon disulfide, CS2
Flammable: 7.9.22 (See: 2.)
Flammable organic chemicals: 15.7.0
Prepare rayon, copper (II), sulfate with ammonia solution "regenerated fibre", "artificial silk":

Carbon disulfide, CS2, carbon bisulfide, Toxic by all routes, Not permitted in schools
Pure carbon disulfide, colourless liquid, pleasant odour like chloroform.
Laboratory carbon disulfide, colourless-yellow liquid, strong, disagreeable cabbage-like odour, highly refractive, slightly soluble in water,
miscible with anhydrous methanol, ethanol, ether, benzene, chloroform, carbon tetrachloride, and oils, fat-solvent properties, highly
flammable, very low flash point, forms explosive mixtures with air, catches fire very easily, dangerous when exposed to heat, flame,
sparks, or friction.
Carbon disulfide reacts with strong oxidizers, sodium, potassium and zinc; azides; rust; halogens; and amines.
It reacts violently with chlorine, nitric oxide, and zinc.
It burns in air with blue flame to form carbon dioxide and sulfur dioxide.
Carbon disulfide is used in manufacture of regenerated cellulose rayon by the viscose process and cellophane.
It was used as grain fumigant in USA until 1985..

16.4.5 Carbon monoxide, C≡O, (note triple bond)
Carbon monoxide, CO, Toxic by inhalation, properties: 3.39.0
Carbon monoxide, Methane with steam: 3.39.1
Carbon monoxide, CO (carbonyl, CO), monodentate, ligand, Toxic by inhalation
Do not prepare in the laboratory!
Carbon monoxide, Solution < 3%, Not hazardous
Catalytic conversion of nitric oxide, (nitrogen monoxide): 3.44.1
Carbon monoxide, danger of vehicle exhausts, tailpipe gases: 18.6.3
Commonly occurring air pollutants, safe air and clean air: (See: carbon monoxide)
Danger of vehicle exhausts, tailpipe gases: 18.6.3
Decomposition of oxalic acid: 3.30.10
Heat carbon with steam, water gas:
Methanoic acid (formic acid) ionization reaction:
Nicotine, tobacco smoking and chewing: 11.11.16 (See 5 and 6.)
Oxides, acidic oxides and basic oxides: 12.17.0
Phosphorus pentoxide: With formic acid forms highly toxic carbon monoxide gas.
Potassium ferrocyanide: Heating with concentrated sulfuric acid forms carbon monoxide gas.
Prepare gases by destructive distillation of coal: 10.6.5
Reactions of methane with steam: 3.39.1
Reduction occurs when: 15.2.02
Tests for gases from burning hydrocarbons, oxyacetylene welding:
Tests for substances with hot concentrated sulfuric acid, note gas formed: (See: 8 and 9). Carbonates
Carbonates are salts or esters of carbonic acid.
Acids and metal carbonates, insoluble carbonates, prepare salts: 2.4
Carbonated water, carbonic acid, H2CO3, soda water: 3.34.3a
Carbonates, CO32-, mineral carbonates: 35.19.2
Decomposition of carbonates: 3.30.1
Dilute acids with carbonates, common carbonates:
Heat carbonates of Cu, Mg, Na, Pb, Zn: 12.16.3
List of carbonates: 1.11
Prepare carbon dioxide, heat carbonates: 13.7.6
Prepare rayon, basic copper carbonate with ammonia solution:
Reactions of carbonates: 12.16.0
Tests for carbonates: Oxyacetylene welding, (oxy-acetylene welding)
In excess air, acetylene (ethyne), burns with a hot white flame.
If the acetylene is mixed with oxygen from separate gas cylinders in an oxy-acetylene torch, a temperature of 3 500oC can be
produced to allow welding of tubes and pipes.
The two ends of the metal objects to be welded are heated until they begin to melt.
Rods of "filler" metal are melted along the joint then the joint cools and solidifies.
The oxyacetylene flame can burn under water.
Also, metal can be preheated with the oxyacetylene flame then cut with a pure oxygen flame.
2C2H2 (g) + 5O2 (g) ---> 4CO2 (g) + 2H2O (g)
Commercial products
Arc welding electrodes, Satin craft 13, 5 kg, 3.2 mm, 380 mm, pack
Arc welding electrodes, Satin craft 13, 5 kg, 2.5 mm, 300 mm, pack
Arc welding electrodes, GP 6012, 5 kg, 3.2 mm, 380 mm, pack
Arc welding electrodes, GP 6012, 5 kg, 2.5 mm, 300 mm, pack
Arc welding mig wires, automatic, autocraft LWI, 15 kg spool, 0.9 mm
Welding gloves, chrome leather, black and gold
Welding goggles, for oxy-acetylene welding, lift up front
Welding helmet, lift up front, head harness
Welding mats, anti-fatigue, non-slip mats, resistant to welding sparks, 700 mm x 800 mm centre piece
Welding mats, anti-fatigue, non-slip mats, resistant to welding sparks, 700 mm x 800 mm end piece
Welding safety apron, chrome leather, reinforced straps, 910 mm x 560 mm
Wire / scratch brush, four rows of steel bristles with wooden handle. Charcoal
See: Charcoal Elements, Compounds, (Commercial)
Charcoal, activated charcoal, charcoal powder, charcoal animal powder, charcoal blocks & drawing sticks
Charcoal, animal charcoal, bone black
Absorb impurities on charcoal, test with litmus: 10.1.1
Activated carbon, activated charcoal (commercial information): 11.0
Activated carbon, prepare sugar crystals from brown sugar: 3.1.10
Charcoal blocks: 35.41.1
Clean dirty water with charcoal: 10.1.2
Drink-can charcoal burner: 22.1.2
Prepare wood gas and wood tar: 16.10.4
Separate by adsorbing impurities: 10.1.0
Heat substances with charcoal and fusion mixture:

Alkannin, C16H16O5, napthoquinone derivative, E103 food colouring but no longer approved, in Dyer's alkanet
as alkanet root extract. Left-handed and right-handed structural forms, D-sugars and L-sugars
See diagram Monosaccharides, D-sugar and L-sugar
The Fischer projection formula invented by Emil Fischer (1852 - 1919), allows the three-dimensional sugar and amino acid molecules
be represented by two-dimensional diagrams on the page.
Horizontal lines show groups projecting above the plane of the page towards you.
Vertical lines show groups projecting below the plane of the page away from you.
So D-glyceraldehyde has the hydroxyl group on C2 on the right and L-glyceraldehyde has the hydroxyl group on C2 on the left,
(Latin: dextro = right, laevo = left).
For all other carbohydrates, if the carbon atom farthest from the aldehyde or ketone group has the same arrangement as
D-glyceraldehyde, hydroxyl on the right of C2, then the compound is a D-sugar.
Similarly, if this "remote carbon atom" has the same arrangement as L-glyceraldehyde, the compound is an L-sugar.
However, monosaccharides exist mainly as cyclic forms, not the aldo-forms or keto-forms.

See diagram Fischer projection and Haworth projection of glucose
The cyclic structure of monosaccharides is shown by a "Haworth projection", invented by W N Haworth, 1813-1950, England.
The oxygen atom is at the upper right and the carbon atoms are arranged clockwise with C1 at the far right.
The hydroxyl groups on the right in the Fischer projection are down in the Haworth projection, so the hydroxyl groups on the left in
the Fischer projection are up in the Haworth projection.
The terminal -CH2OH group is up in the Haworth projection for D-sugars, and down for L-sugars.
D-glucose can have α-or β-forms, depending on the position of the hydroxyl group attached to C1, down in the α-form and up in the
Most monosaccharides have a ring cycle of six atoms, one oxygen atom and five carbon atoms, called the pyranose form.
A ring cycle of 5 atoms, one oxygen atom and four carbon atoms is called a furanose form.
So D-fructose can exist as α-D-fructofuranose, -OH on C2 is down, and β-D-fructofuranose, -OH on C2 is up.
Glucose, Sold as: "D-(+)-Glucose, dextrose"
Fructose, D form, but laevorotatory, so "L-fructose", Sold as: "D-(-)-Fructose, D-Levulose, Fruit sugar".