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Sigma-Aldrich

(±)-L-Alliin

≥90% (HPLC)

Synonym(s):

ACSO, SAC, S-Allyl-L-cysteine sulfoxide

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About This Item

Empirical Formula (Hill Notation):
C6H11NO3S
CAS Number:
17795-26-5
Molecular Weight:
177.22
Beilstein:
1724805
EC Number:
241-773-6
MDL number:
MFCD00151977
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57652509
NACRES:
NA.26

Quality Level

100

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

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.
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
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
S.S. Singh et al.
J. Med. Aromat. PlantSci., 20, 93-93 (1998)
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
Balmiki Ray et al.
Journal of neurochemistry, 117(3), 388-402 (2010-12-21)
Alzheimer's disease (AD) is one of the most common forms of dementia in the elderly. In AD patients, β-amyloid peptide (Aβ) plaques and neurofibrillary tangles are common features observed in the CNS. Aβ deposition results in the production of reactive
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