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S-Allylcysteine

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S-Allyl cysteine
S-Allyl cysteine
S-Allyl cysteine
Names
IUPAC name (R)-2-Amino-3-prop-2-enylsulfanylpropanoic acid
Other names S-2-propenyl-L-cysteine; S-allyl-laevo-cysteine; S-allylcysteine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations SAC
ChemSpider
ECHA InfoCard 100.166.686 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1Key: ZFAHNWWNDFHPOH-YFKPBYRVSA-N
  • InChI=1/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1Key: ZFAHNWWNDFHPOH-YFKPBYRVBL
SMILES
  • O=C(O)(N)CSC\C=C
Properties
Chemical formula C6H11NO2S
Molar mass 161.22 g/mol
Density 1.191 ± 0.06 g/cm
Melting point 219 to 220 °C (426 to 428 °F; 492 to 493 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

S-Allylcysteine (SAC) is an organosulfur compound that has the formula HO2CCH(NH2)CH2SCH2C=CH2. It is the S-allylated derivative of the amino acid cysteine. As such only the L-enantiomer is significant biologically. SAC constituent of aged garlic. A number of related compounds are found in garlic, including the disulfide S-"allylmercaptocysteine" (SAMC, HO2CCH(NH2)CH2SSCH2C=CH2) and γ-glutamyl-S-allylcysteine" (GSAC).

Allylcysteine is of interest for its potential medicinal properties. and as a chemopreventive.

See also

  • Alliin, the S-oxide of allyl cysteine

References

  1. Fujii, Takuto; Matsutomo, Toshiaki; Kodera, Yukihiro (2018). "Changes of S-Allylmercaptocysteine and γ-Glutamyl-S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process". Journal of Agricultural and Food Chemistry. 66 (40): 10506–10512. doi:10.1021/acs.jafc.8b02541. PMID 30226990. S2CID 52297055.
  2. Yeh YY, Liu L (2001). "Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies". Journal of Nutrition. 131 (3s): 989S – 93S. doi:10.1093/jn/131.3.989S. PMID 11238803.
  3. Arora, Annu; Tripathi, Chitra; Shukla, Yogeshwer (2005). "Garlic and its organosulfides as potential chemopreventive agents: a review". Current Cancer Therapy Reviews. 1 (2): 199–205. doi:10.2174/1573394054021772.

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