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Ajoene information


Ajoene
Names
Preferred IUPAC name
(1E)-3-(Prop-2-ene-1-sulfinyl)-1-[(prop-2-en-1-yl)disulfanyl]prop-1-ene
Identifiers
CAS Number
  • 92285-01-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL122890 checkY
ChemSpider
  • 4533332 checkY
PubChem CID
  • 5386591
UNII
  • 99A0041VG8 checkY
CompTox Dashboard (EPA)
  • DTXSID501318485 Edit this at Wikidata
InChI
  • InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+ checkY
    Key: IXELFRRANAOWSF-FNORWQNLSA-N checkY
  • InChI=1/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+
    Key: IXELFRRANAOWSF-FNORWQNLBE
SMILES
  • O=S(C/C=C/SSC/C=C)C\C=C
Properties
Chemical formula
C9H14OS3
Molar mass 234.39 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ajoene /ˈɑːh.n/ is an organosulfur compound found in garlic (Allium sativum) extracts. It is a colorless liquid that contains sulfoxide and disulfide functional groups. The name[1] (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four stereoisomers, which differ in terms of the stereochemistry of the central alkene (E- vs Z-) and the chirality of the sulfoxide sulfur (R- vs S-).

  1. ^ Block E, Ahmad S, Jain MK, Crecely R, Apitz-Castro R, Cruz MR (1984). "(E,Z)-Ajoene: A potent antithrombotic agent from garlic". Journal of the American Chemical Society. 106 (26): 8295–8296. doi:10.1021/ja00338a049.

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Ajoene

Last Update:

Ajoene /ˈɑːhoʊ.iːn/ is an organosulfur compound found in garlic (Allium sativum) extracts. It is a colorless liquid that contains sulfoxide and disulfide...

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Garlic

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Fresh or crushed garlic yields the sulfur-containing compounds allicin, ajoene, diallyl polysulfides, vinyldithiins, and S-allylcysteine, as well as enzymes...

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Alliin

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(DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene. Garlic powder is not a source of alliin, nor is fresh garlic upon maceration...

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Glutathione reductase

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PDB gallery 1bwc: STRUCTURE OF HUMAN GLUTATHIONE REDUCTASE COMPLEXED with AJOENE INHIBITOR AND SUBVERSIVE SUBSTRATE 1dnc: HUMAN GLUTATHIONE REDUCTASE MODIFIED...

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Sulfoxide

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dimethylsulfide. Naturally-occurring chiral sulfoxides include alliin and ajoene. Gama Á, Flores-López LZ, Aguirre G, Parra-Hake M, Hellberg LH, Somanathan...

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Organosulfur chemistry

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hydrogenolysis of thiophene: C4H4S + 8 H2 → C4H10 + H2S Compounds like allicin and ajoene are responsible for the odor of garlic. Lenthionine contributes to the flavor...

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Vinyldithiin

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solvents, among the compounds formed are the isomeric vinyldithiins and ajoene. As shown in the Scheme, allicin (1) decomposes into 2-propenesulfenic acid...

Word Count : 756

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