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Allicin information


Allicin
Structural formula of R-allicin
Ball and stick model of R-allicin
Names
Preferred IUPAC name
S-(Prop-2-en-1-yl) prop-2-ene-1-sulfinothioate
Other names
2-Propene-1-sulfinothioic acid S-2-propenyl ester
3-[(Prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
S-Allyl prop-2-ene-1-sulfinothioate
Identifiers
CAS Number
  • 539-86-6 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
1752823
ChEBI
  • CHEBI:28411 checkY
ChEMBL
  • ChEMBL359965 checkY
ChemSpider
  • 58548 checkY
ECHA InfoCard 100.007.935 Edit this at Wikidata
EC Number
  • 208-727-7
IUPHAR/BPS
  • 2419
KEGG
  • C07600 checkY
MeSH Allicin
PubChem CID
  • 65036
UNII
  • 3C39BY17Y6 checkY
CompTox Dashboard (EPA)
  • DTXSID6043707 Edit this at Wikidata
InChI
  • InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2 checkY
    Key: JDLKFOPOAOFWQN-UHFFFAOYSA-N checkY
  • InChI=1/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
    Key: JDLKFOPOAOFWQN-UHFFFAOYAO
SMILES
  • O=S(SC\C=C)C\C=C
  • C=CCSS(=O)CC=C
Properties
Chemical formula
C6H10OS2
Molar mass 162.26 g·mol−1
Appearance Colourless liquid
Density 1.112 g cm−3
Melting point < 25 °C (77 °F; 298 K)
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Allicin is an organosulfur compound obtained from garlic.[1] When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic.[2] Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide.[3] Allicin is an antifeedant, i.e. the defense mechanism against attacks by pests on the garlic plant.[4]

Allicin is an oily, slightly yellow liquid that gives garlic its distinctive odor. It is a thioester of sulfenic acid. It is also known as allyl thiosulfinate.[5] Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.[6]

  1. ^ Block E (March 1985). "The Chemistry of Garlic and Onions". Scientific American. 252 (3): 114–9. Bibcode:1985SciAm.252c.114B. doi:10.1038/scientificamerican0385-114. PMID 3975593.
  2. ^ Kourounakis PN, Rekka EA (November 1991). "Effect on active oxygen species of alliin and Allium sativum (garlic) powder". Research Communications in Chemical Pathology and Pharmacology. 74 (2): 249–52. PMID 1667340.
  3. ^ Ilic D, Nikolic V, Nikolic L, Stankovic M, Stanojevic L, Cakic M (2011). "Allicin and related compounds: Biosynthesis, synthesis and pharmacological activity" (PDF). Facta Universitatis. 9 (1): 9–20. doi:10.2298/FUPCT1101009I.
  4. ^ Borlinghaus J, Albrecht F, Gruhlke MC, Nwachukwu ID, Slusarenko AJ (August 2014). "Allicin: chemistry and biological properties". Molecules. 19 (8): 12591–618. doi:10.3390/molecules190812591. PMC 6271412. PMID 25153873.
  5. ^ Nikolic V, Stankovic M, Nikolic L, Cvetkovic D (January 2004). "Mechanism and kinetics of synthesis of allicin". Die Pharmazie. 59 (1): 10–4. PMID 14964414.
  6. ^ Rabinkov A, Miron T, Konstantinovski L, Wilchek M, Mirelman D, Weiner L (February 1998). "The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins". Biochimica et Biophysica Acta (BBA) - General Subjects. 1379 (2): 233–44. doi:10.1016/s0304-4165(97)00104-9. PMID 9528659.

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Allicin

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Allicin is an organosulfur compound obtained from garlic. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which...

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Garlic

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heat in foods. The process of cooking garlic removes allicin, thus mellowing its spiciness. Allicin, along with its decomposition products diallyl disulfide...

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prop-2-ene-1-sulfinothioate, commonly called Allicin. Fresh garlic has little odor until it is chopped or crushed. Allicin is produced from alliin (a derivative...

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Alliin

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the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin and other thiosulfinates in garlic are unstable...

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Diallyl disulfide

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disulfide, allicin, was discovered in 1944 by Chester J. Cavallito and John Hays Bailey. In 1947, A. Stoll and E. Seebeck found that allicin in turn can...

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Elephant garlic

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using a DART ion source, elephant garlic has been shown to produce both allicin, found in garlic, and syn-propanethial-S-oxide (onion lachrymatory factor)...

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Piperine

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active piquant chemical in mustard, radishes, horseradish, and wasabi Allicin, the active piquant flavor chemical in raw garlic and onions (see those...

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Vinyldithiin

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3-dithiin, are organosulfur phytochemicals formed in the breakdown of allicin from crushed garlic (Allium sativum). Vinyldithiins are Diels-Alder dimers...

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Pungency

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pungent feeling caused by allyl isothiocyanate, capsaicin, piperine, and allicin is caused by activation of the heat thermo- and chemosensitive TRP ion...

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Allyl alcohol

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(producing from garlic in two ways: firstly by a self-condensation reaction of allicin and its decomposition products such as diallyl trisulphide and diallyl...

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Organosulfur chemistry

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decreasing order of their occurrence. Illustrative organosulfur compounds Allicin, the active flavor compound in crushed garlic (R)-Cysteine, an amino acid...

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Chester John Cavallito

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disulfide) and antibiotic activity of a compound he named allicin. Cavallito established that allicin was a member of a class of organosulfur compounds known...

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Allyl isothiocyanate

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chemical in black pepper Capsaicin, the piquant chemical in chili peppers Allicin, the piquant flavor chemical in raw garlic Everaerts, W.; Gees, M.; Alpizar...

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Vacuole

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garlic, alliin and the enzyme alliinase are normally separated but form allicin if the vacuole is broken. A similar reaction is responsible for the production...

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Sulbutiamine

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conducted in the 1950s, mainly in Japan. These efforts led to the discovery of allicin (diallyl thiosulfinate) in garlic, which became a model for medicinal chemistry...

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Sulfur

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Biotin or vitamin B7 Penicillin, an antibiotic ("R" is the variable group) Allicin, a chemical compound in garlic Diphenyl disulfide, a representative disulfide...

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Thyme

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404...

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Antifeedant

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"The Pungency of Garlic: Activation of TRPA1 and TRPV1 in Response to Allicin" (PDF). Current Biology. 15 (10): 929–34. doi:10.1016/j.cub.2005.04.018...

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Aglio Rosso di Nubia

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University of Palermo showed that the Nubia red garlic has a content of allicin well above average. This gives it a particularly intense flavor. It is...

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Onion

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404...

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Ruta graveolens

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Turmeric

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Rosemary

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Nicotine

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404...

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Clove

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Tramadol

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Cannabidiol

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Horseradish

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Sichuan pepper

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