All Photos(1)

74264

Sigma-Aldrich

(±)-L-Alliin

≥90% (HPLC)

Synonym(s):
ACSO, SAC, S-Allyl-L-cysteine sulfoxide
Empirical Formula (Hill Notation):
C6H11NO3S
CAS Number:
Molecular Weight:
177.22
Beilstein:
1724805
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥90% (HPLC)

form

powder or crystals

color

white to faint beige

storage temp.

−20°C

SMILES string

N[C@@H](CS(=O)CC=C)C(O)=O

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

InChI key

XUHLIQGRKRUKPH-ITZCMCNPSA-N

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General description

Alliin is the precursor of allicin.
Constituent of garlic (Allium sativum)

Application

(±)-L-Alliin has been used in nutrient broth No. 2 (NB2) for determining the concentrations of garlic-derived products active against Clostridium jejuni.

Biochem/physiol Actions

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.
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.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Amaj A Laskar et al.
Current pharmaceutical biotechnology, 20(6), 506-516 (2019-05-01)
Lower human salivary aldehyde dehydrogenase (hsALDH) activity increases the risk of aldehyde mediated pathogenesis including oral cancer. Alliin, the bioactive compound of garlic, exhibits many beneficial health effects. To study the effect of alliin on hsALDH activity. Enzyme kinetics was...
P Todd Stukenberg et al.
Chromosoma, 124(4), 463-480 (2015-04-29)
Kinetochores generate a signal that inhibits anaphase progression until every kinetochore makes proper attachments to spindle microtubules. This spindle assembly checkpoint (SAC) increases the fidelity of chromosome segregation. We will review the molecular mechanisms by which kinetochores generate the SAC...
A Rabinkov et al.
Biochimica et biophysica acta, 1379(2), 233-244 (1998-04-07)
Allicin (thio-2-propene-1-sulfinic acid S-allyl ester) is the main biologically active component of garlic clove extracts. Its biological activity was attributed to either antioxidant activity or thiol disulfide exchange. Antioxidant properties of both allicin and its precursor, alliin (+S-allyl-L-cysteine sulfoxide), were...
Linda J W Shimon et al.
Journal of molecular biology, 366(2), 611-625 (2006-12-19)
Alliinase (alliin lyase EC 4.4.1.4), a PLP-dependent alpha, beta-eliminating lyase, constitutes one of the major protein components of garlic (Alliium sativum L.) bulbs. The enzyme is a homodimeric glycoprotein and catalyzes the conversion of a specific non-protein sulfur-containing amino acid...
S.S. Singh et al.
J. Med. Aromat. PlantSci., 20, 93-93 (1998)

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