Garlic Super function Magic applications.

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Constituents and Phytochemicals of Garlic.Allium sativum L.

Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image Garlic contains volatile oil with sulphur containing compounds (notably allicin, alliin and ajoene); enzymes, B vitamins, Minerals, flavonoids.

The undamaged garlic is without odour, but on cutting or pressing it, strongly odoriferous and chemically reactive sulphur compounds are immediately generated. This mechanism protects the garlic against parasites and moulds, and is due to an enzymatic generation of allicin (diallyl disulphide sulphoxide) from the stable compound alliin (S-allyl-L-cystein sulphoxide). The odour of freshly cut garlic comes from allicin. Further reaction may result in additional powerful odorant like diallyl disulphide and vinyl-[4H]-dithiines. The enzyme alliinase is denatured by short heating, and therefore preserved garlic has a mild taste. Garlic's sulphur compounds are antibacterial and antioxidative, and their medicinal benefits are still being investigated.
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Enzymatic generation of allicin from alliin and its further reaction into diallyl disulphide and vinyl-dithiines:

Garlic Compounds

Present in this species is S-2-propenyl-L-cysteine sulfoxide, otherwise known as alliin. Damage to the plant results in the breakdown of alliin by the co-occurring enzyme alliinase to produce allicin. The allicin then undergoes a series of disproportionation reactions and also enzymatically catalysed reductions to produce various sulfur-containing oils and allyl alcohol. These products are more or less volatile and are responsible in part for the odour of garlic (Brodnitz et al. 1971, Freeman and Whenham 1976). Diallyl di- and tri- sulfides are the principal constituents of the resulting oil.
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Diallyldisulfide is considered to be the major allergen of garlic oil (Hjorth and Roed-Petersen 1976). Garlic oil has also been reported to induce irritation and vesication of the skin (White 1887, Burkill 1935). Nadkarni (1976) notes that the juice from garlic cloves may be used as a rubefacient liniment. Garlic juice produces superficial irritation of the skin which, although it results in rubefaction and vesication, does not penetrate the underlying tissues (Watt and Breyer-Brandwijk 1962). Vohora et al. (1973) also report that garlic applied externally acts as a rubefacient. Strobel et al. (1978) describe dermatitis produced by a poultice containing garlic. Neves (1964) and Martinescu (1981) have also reported contact dermatitis from the plant. In Mexico, garlic appeared to cause photosensitisation after it had been applied to a variety of dermatoses including lichen simplex and acne (Cueva Duran 1955, Saul 1972). Lesions developed on sun-exposed sites including some to which garlic had not been deliberately applied.

A self-inflicted bullous eruption on the shins produced by garlic in a malingerer resembled pemphigus both histologically and cytologically (Pirogova Katyukhina 1970).

Inhibition of platelet aggregation has been shown to occur following ingestion of fresh garlic cloves (Boullin 1981). This property has been found to be associated with methylallyltrisulfide, a minor constituent of garlic oil (Ariga et al. 1981).

Chromatogram for INA allicin in garlic method
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Differentiation of Allicin and Alliin

Alliin

Alliin (S-allylcysteine sulfoxide), is constructed of an allyl group (green), a sulfoxide group (yellow), and the amino acid cysteine (purple - in its regular form, contains -SH rather than S=O). Alliin is biosynthesized from its parent compound, S-Allylcysteine (deoxyalliin). It is by far the most abundant of the four cysteine sulfoxides known to be present in whole, unbruised Garlic and in properly dried powders. Whole Garlic contains from 6 to 14 milligrams of alliin per gram, fresh weight, and from 18 to 42 mg/g dry weight (a typical fresh Garlic clove weighs 2-4 g, and so would contain 12-56 mg of alliin; it also contains about 65% water, hence the higher concentration of alliin in dry Garlic).Analyses of Garlic powder tablets have revealed a wide range of alliin concentrations: from a low of 0.4 up to 24 mg per gram of tablet. "Allicin-standardized" tablets contain an average of 13 mg/g of alliin, while non-standardized tablets contain, on average, 7 mg/g.

To preserve the maximum amount of alliin in dried products, the cloves should be minimally sliced and carefully freeze-dried. Too much slicing mixes more alliin and alliinase, resulting in increased allicin production prior to dehydration; the unstable allicin soon degrades. Additionally, excess heat during dehydration inactivates the alliinase, destroying the allicin-yield potential of the product. After the powdering process, the remaining alliin and alliinase are quite stable as long as the powder is kept dry and reasonably cool. The average five-year storage loss of allicin-yield is 36%.2

Alliin is quite stable in the absence of active alliinase, and can also be found in cooked Garlic (if it has not been converted to allicin before cooking), Garlic vinegars, and aged extracts.

Alliin has demonstrated antioxidant activity in some studies,but not in others. Its parent compound, S-allylcysteine, is a proven antioxidant, as is its derivative, allicin.

Allicin
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Allicin (Diallyl thiosulfinate), is constructed from two allyl groups (green), and a thiosulfinate group (yellow). It is biosynthesized from two molecules of alliin (or from its close relative, methiin - methylcysteine sulfoxide) by the enzyme alliinase. Allicin makes up about 60-90% of the total thiosulfinates in crushed Garlic.

The total allicin-yield has been calculated as 2.5 - 5.1 mg/g of fresh, crushed Garlic or about 5 to 20 mg per clove. For dried Garlic powder tablets, allicin-yield is determined by subjecting the product to simulated gastrointestinal conditions, including agitation in simulated stomach acid (pH 1.5) followed by agitation in simulated intestinal fluid (pH 7.5). One respected brand of enteric-coated supplement claims to release 3.2 mg of allicin per 350 mg Garlic powder, or 9.1 mg/g of product. This falls within the range of the natural allicin potential in one clove of Garlic.

Once formed, allicin is unstable; pure allicin at room temperature has a half-life of 2-16 hours; in garlic juice or crushed garlic, 2.4 days; in garlic juice diluted 1:10 in water, 22 days. Refrigeration increases the life of allicin by a factor of twenty. This indicates that while allicin is not stable enough for commercial use, its medicinal properties can be taken advantage of in home herbal preparations.

Allicin has a low solubility in water, around 2%. In air or water, it degrades to sulfides including diallyl disulfide, diallyl trisulfide, and allyl methyl trisulfide. Steam distillation (to make Garlic oil) produces these and at least twenty other sulfides. In oil macerates (such as Garlic minced in olive oil), allicin transforms to sulfides, ajoene, and vinyldithiins. These compounds are physiologically active as well; in many cases, allicin itself is not directly responsible for medicinal effects, but its transformation products are. Synergistic effects are likely.

For more information on the transformation products of allicin and the gamma-Glutamylcysteines (including S-allylcysteine), go to the Advanced page.

The constituents in garlic are protein; volatile oil; vitamins A, B1, B2, and C; calcium; copper; germanium; iron; magnesium; manganese; phosphorous; phytoncides; potassium; selenium; sulfur; unsaturated aldehydes; zinc;and enzymes.

The volatile oil is made up of the sulfur-containing compounds allicin, diallyl disulfide, diallyl trisulfide, alliin, and S-methyl-L-cysteine sulfoxide. These sulfur-containing compounds are generally thought to be the active principles that give garlic its health benefits as well as its strong odor, but the trace minerals and vitamins also play an important part.

Probably the most beneficial compound is allicin, which is made by the enzyme alliinase breaking down alliin to allicin. This process is essential to garlic's potency. Heating or cooking garlic inactivates the enzyme, but if garlic is chopped first and allowed to sit for 10 minutes before cooking, the enzyme has a chance to do its job and enough allicin is formed to maintain the healthful benefits.The same is true when roasting garlic bulbs. The top should be cut off and the bulb stabbed a few times and then left for 10 minutes before roasting. Of course, using garlic raw ensures its health qualities.

Phytochemicals of Garlic:

Bulb Flower Leaf Shoot Content:BETA-CAROTENE,NIACIN,RIBOFLAVIN,THIAMIN
Leaf Content:ORNITHINE

Plant Content: 24-METHYLENE-CYCLOARTENOL,ALLISATIN,BETA-SITOSTEROL,CHLOROGENIC-ACID,GAMMA-L-GLUTAMYL-L-VALINE,GAMMA-L-GLUTAMYL-S-(2-CARBOXY-1-PROPYL)-,CYSTEINEGLYCINE,KAEMPFEROL,LINOLENIC-ACID,OLEANOLIC-ACID,OLEIC-ACID,P-HYDROXY-BENZOIC-ACID,PHLOROGLUCINOL,PHYTIC-ACID,QUERCETIN-3-O-BETA-D-GLUCOSIDE,RUTIN,SINAPIC-ACID,STIGMASTEROL,SUCCINIC-ACID,TAURINE,VIT-U

Bulb Content:GAMMA-L-GLUTAMYL-METHIONINE;1,2-(PROP-2-ENYL)-DISULFANE;1,2-DIMERCAPTOCYCLOPENTANE;1,2-EPITHIOPROPANE;1,3-DITHIANE;1-HEXANOL;1-METHYL-1,2-(PROP-2-ENYL)-DISULFANE;1-METHYL-2-(PROP-2-ENYL)-DISULFANE;1-METHYL-3-(PROP-2-ENYL)-TRISULFANE;2,3,4-TRITHIAPENTANE;2,5-DIMETHYL-TETRAHYDROTHIOPHENE;2-METHYL-BENZALDEHYDE;2-PROPEN-1-OL;2-VINYL-4H-1,3-DITHIIN;3,5-DIETHYL-1,2,4-TRITHIOLANE;3-METHYL-2-CYCLOPENTENE-1-THIONE;3-VINYL-4H-1,2-DITHIIN;4-METHYL-5-VINYLTHIAZOLE;5-BUTYL-CYSTEINE-SULFOXIDE;ADENOSINE;AJOENE;ALANINE;ALLICIN;ALLIIN;ALLIINASE;ALLISTATIN-I;ALLISTATIN-II;ALLIXIN;ALLYL-DISULFIDE;ALLYL-METHYL-DISULFIDE;ALLYL-METHYL-TRISULFIDE;ALLYL-PROPYL-DISULFIDE;ALPHA-PHELLANDRENE;ALPHA-PROSTAGLANDIN-F-1;ALPHA-PROSTAGLANDIN-F-2;ALPHA-TOCOPHEROL;ANILINE;ARACHIDONIC-ACID;ARGININE;BETA-PHELLANDRENE;BETA-TOCOPHEROL;BIOTIN;CAFFEIC-ACID;CHOLINE;CIS-AJOENE;CITRAL;CYCLOALLIIN;CYSTINE;DESGALACTOTIGONIN;DESOXYRIBONUCLEASE;DIALLYL-DISULFIDE;DIALLYL-SULFIDE;DIALLYL-TETRASULFIDE;DIALLYL-TRISULFIDE;DIGALACTOSYL-DIGLYCERIDE;DIMETHYL-DIFURAN;DIMETHYL-DISULFIDE;DIMETHYL-SULFIDE;DIMETHYL-TRISULFIDE;EICOSAPENTAENOIC-ACID;FERULIC-ACID;FOLIACIN;GAMMA-L-GLUTAMYL-ISOLEUCINE;GAMMA-L-GLUTAMYL-L-LEUCINE;GAMMA-L-GLUTAMYL-L-PHENYLALANINE;GAMMA-L-GLUTAMYL-S-ALLYL-CYSTEINE;GAMMA-L-GLUTAMYL-S-ALLYL-MERCAPTO-CYSTEINE;GAMMA-L-GLUTAMYL-S-BETA-CARBOXY-BETA-;METHYL-ETHYL-CYSTEINYL-GLYCINE;GAMMA-L-GLUTAMYL-S-METHYL-L-CYSTEINE- SULFOXIDE;GAMMA-L-GLUTAMYL-S-PROPYL-L-CYSTEINE;GERANIOL;GIBBERELLIN-A-3;GIBBERELLIN-A-7;GITONIN;GLUTATHIONE;GLYCEROL-SULFOQUINOVOSIDE;GLYCINE;GUANOSINE;HEXA-1,5-DIENYL-TRISULFIDE;HEXOKINASE;HISTIDINE;ISOBUTYL-ISOTHIOCYANATE;ISOLEUCINE;LEUCINE;LINALOL;LYSINE;METHIONINE;METHYL-ALLYL-DISULFIDE;METHYL-ALLYL-SULFIDE;METHYL-ALLYL-TRISULFIDE;METHYL-PROPYL-DISULFIDE;MONOGALACTOSYL-DIGLYCERIDE;MYROSINASE;NICOTINIC-ACID;P-COUMARIC-ACID;PHENYLALANINE;PHOSPHATIDYL-CHOLINE;PHOSPHATIDYL-ETHANOLAMINE;PHOSPHATIDYL-INOSITOL;PHOSPHATIDYL-SERINE;PROLINE; PROP-2-ENYL-DISULFANE;PROPENE;PROPENETHIOL;PROSTAGLANDIN-A-1;PROSTAGLANDIN-A-2;PROSTAGLANDIN-B-1;PROSTAGLANDIN-B-2;PROSTAGLANDIN-E-1;PROSTAGLANDIN-E-2;PROTODEGALACTOTIGONIN;PROTOERUBOSIDE-B;PSEUDOSCORIDININE-A;PSEUDOSCORIDININE-B;QUERCETIN;RAFFINOSE;S-(2-CARBOXY-PROPYL)-GLUTATHIONE;S-ALLO-MERCAPTO-CYSTEINE;S-ALLYL-CYSTEINE;S-ALLYL-CYSTEINE-SULFOXIDE;S-ETHYL-CYSTEINE-SULFOXIDE;S-METHYL-CYSTEINE;S-METHYL-CYSTEINE-SULFOXIDE;S-METHYL-L-CYSTEINE-SULFOXIDE;S-PROPENYL-CYSTEINE;S-PROPYL-CYSTEINE-SULFOXIDE;SAPONIN;SATIVOSIDE-B-1;SATIVOSIDE-R-1;SATIVOSIDE-R-2;SCORDINE;SCORDININ-A;SCORODININ-A-1;SCORODININ-A-2;SCORODININ-B;SCORODININE-A-3;SCORODOSE;SERINE;THIAMACORNINE;THIAMAMIDINE;THREONINE;TRANS-1-PROPENYL-METHYL-DISULFIDE;TRANS-AJOENE;TRANS-S-(PROPENYL-1-YL)-CYSTEINE-DISULFIDE;TRYPTOPHAN;TYROSINASE;TYROSINE;VALINE,etc.

Wire frame Representation of Allicin/Space fill Representation of Allicin
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Allicin - the smell of health

Have you ever wondered what causes the smell of garlic? You guessed it, it's allicin! But, I hear you ask, what is allicin? Well, read on and all will become clear!

Allicin (C6H10OS2) is an oily, yellow liquid, which as you will have probably guessed by now, gives garlic its characteristic odour which is due to the SO group. It also has a range of medical properties.
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Reactions and synthesis

Allicin is synthesised from alliin (see above) when garlic is crushed or bruised. The reaction is catalysed by an enzyme, alliinase, and as a result quite complex. Allicin is a very reactive compound. It is slightly soluble in water and soluble in alcohol, which is what would be expected of an organic molecule containing OH. It decomposes on heating. In the body, it oxidises the haemoglobin in the blood to methemoglobin.
Garlic Extract INCI Name ALLIUM SATIVUM EXTRACT EINECS ELINCS No.:232-371-1 CAS 8008-99-9 Garlic Bulb Extract Allicin photo picture image

Being a strongly oxidising compound, it protects garlic from attack by bacteria and insects by disabling the enzymes that are found in the substrate necessary for infections to occur, thus acting as a natural insecticide. It does so by attacking the SH groups found on their active sites. This is also the case for proteinases and alcohol dehydrogenases, enzymes that promote invasion and infection of bacteria in the human body. It is therefore believed that allicin is a good natural cure-all. Studies show that prolonged exposure to this chemical can have such benefits as: lowering incidence of stomach cancer, lenghtening of blood clotting times and reduction of blood lipid levels.

Allicin also belongs to the family of phytochemicals, which are believed to be useful in cancer treatement and cure. Studies are under way to test their effectiveness. Other studies, however appear to show that it is not the allicin but also other chemicals present in garlic which lead to these properties.