(2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid

• ChemBase ID: 125682
• Molecular Formular: C6H11NO3S
• Molecular Mass: 177.22144
• Monoisotopic Mass: 177.04596422
• SMILES: O=S(CC=C)C[C@@H](C(=O)O)N
• Canonical SMILES: N[C@H](C(=O)O)CS(=O)CC=C
• InChI: InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m0/s1
• InChIKey: XUHLIQGRKRUKPH-ITZCMCNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
• IUPAC Traditional name: 3-(allylsulfinyl)alanin
• Synonyms: 3-(2-Propenylsulfinyl)alanine; (S)-3-(2-Propenylsulfinyl)-L-alanine; 3-((S)-Allylsulfinyl)-L-alanine; S-Allyl-L-cysteine sulfoxide; Alliin; ACSO; S-Allyl-L-cysteine sulfoxide; SAC; (±)-L-Alliin

Database IDs

• CAS Number: 556-27-4; 17795-26-5
• EC Number: 241-773-6
• MDL Number: MFCD00151977
• Beilstein Number: 1724805
• PubChem SID: 162220032; 24886668
• PubChem CID: 87310
• CHEMBL: 464166
• Chemspider ID: 7850537
• Wikipedia Title: Alliin

CALCULATED PROPERTIES

• Acid pKa: 1.8372514
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.7407596
• LogD (pH = 7.4): -3.7753744
• Log P: -3.7406127
• Molar Refractivity: 43.7226 cm^3
• Polarizability: 17.255266 Å^3
• Polar Surface Area: 80.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in water
• Apperance: White to off white crystalline powder
• Melting Point: 163 - 165°C (325.4 - 329°F)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C6H11NO3S

DETAILS

Sigma Aldrich - 74264

Biochem/physiol Actions
Sulfur-containing amino acid that is converted to allicin by alliinase. Allicin is cytotoxic to several mammalian cancer cell lines and can protect against tumor formation induced by various exogenous chemical carcinogens.
L-Alliin (S-Allyl-L-cysteine sulfoxide) is an amino acid derived from L-cysteine. S-Allyl-L-cysteine Sulfoxide (ACSO) is an anti-atherosclerotic compound with antioxidant and anti-inflammatory activities.
S-Allyl-L-cysteine ((±)-L-Alliin) (SAC) may be used to study its potential as an anti-Alzheimer’s factor. SAC has been shown to increase cell proliferation and neuroblast differentiation by increasing 5-HT(1A) and provide antioxidative benefit to neurons and synapses.
General description
Constituent of garlic (Allium sativum)1
Protocols & Applications
Onion (Allium cepa) Plant Profile: bioactives, mechanism of action, references