S-1-Propenyl-L-cysteine

For research use only. Not for therapeutic Use.

  • CAT Number: I019262
  • CAS Number: 52438-09-2
  • Molecular Formula: C6H11NO2S
  • Molecular Weight: 161.22
  • Purity: ≥95%
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S-1-Propenyl-L-cysteine is a stereoisomer of S-allyl-l-cysteine, extracted from garlic, with immunomodulatory effects and reduces blood pressure in a hypertensive animal model[1]. S-1-Propenyl-L-cysteine exhibits antioxidative efficacy through a NO-dependent BACH1 signaling pathway[2]. S-1-Propenyl-L-cysteine is orally active.
S-1-Propenyl-L-cysteine NO-dependently upregulates levels of HMOX1, which causes the downregulation of BACH1, leads to a BACH1-degradation in nucleus[2].
S-1-Propenyl-L-cysteine inhibites lipopolysaccharides (LPS)-induced TLR4 signaling pathway by inducing MyD88 degradation through its denaturation and the activation of autophagy[4].
S-1-Propenyl-L-cysteine (6.5 mg/kg, p.o.) reduces systolic blood pressure (SBP), alters histidine metabolism and exerts the antihypertensive effect via the central histamine H3 receptor in spontaneously hypertensive rats[3].


Catalog Number I019262
CAS Number 52438-09-2
Synonyms

(2R)-2-amino-3-[(E)-prop-1-enyl]sulfanylpropanoic acid

Molecular Formula C6H11NO2S
Purity ≥95%
InChI InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2+/t5-/m0/s1
InChIKey HYGGRRPFVXHQQW-HRJJCQLASA-N
SMILES CC=CSCC(C(=O)O)N
Reference

[1]. Kodera Y, et al. Chemical and Biological Properties of S-1-Propenyl-l-Cysteine in Aged Garlic Extract. Molecules. 2017 Mar 31;22(4).
 [Content Brief]

[2]. Tsuneyoshi T, et al., S-1-Propenylcysteine augments BACH1 degradation and heme oxygenase 1 expression in a nitric oxide-dependent manner in endothelial cells. Nitric Oxide. 2019 Mar 1;84:22-29.
 [Content Brief]

[3]. Matsutomo T, et al., Metabolomic study reveals the acute hypotensive effect of S-1-propenylcysteine accompanied by alteration of the plasma histidine level in spontaneously hypertensive rats. J Pharm Biomed Anal. 2019 May 10;168:148-154.
 [Content Brief]

[4]. Suzuki JI, et al., Anti-inflammatory action of cysteine derivative S-1-propenylcysteine by inducing MyD88 degradation. Sci Rep. 2018 Sep 20;8(1):14148.
 [Content Brief]

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