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1′-S-1′-Acetoxychavicol Acetate

1′-S-1′-Acetoxychavicol Acetate

Product ID A0917
Cas No. 52946-22-2
Purity ≥98%
Product Unit SizeCostQuantityStock
5 mg $108.00 Please Inquire
10 mg $204.00 Please Inquire
25 mg $424.50 Please Inquire
100 mg $1,267.90 Please Inquire
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  • Description
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Description

1’-(S)-1’-Acetoxychavicol acetate (galangal acetate) displays a wide variety of beneficial properties, including antioxidative, anti-obesity, antibacterial, anti-parasitic, chemopreventative, and chemotherapeutic activities. This compound is best known for its ability to inhibit xanthine oxidase, but also activates transient receptor potential cation channel A1 (TRPA1), an ion channel involved in pain and cold signaling. In vitro, 1’-(S)-1’-Acetoxychavicol acetate decreases GPDH activity and downregulates PPARγ, C/EBPα, and phosphorylated AMPK, inhibiting adipogenesis. Additionally, 1’-(S)-1’-Acetoxychavicol acetate decreases visceral fat mass in animal models. 1’-(S)-1’-Acetoxychavicol acetate displays activity against both gram negative and gram positive bacteria in vitro and anti-parasitic activity against Leishmania donovani. In vitro, 1’-(S)-1’-Acetoxychavicol acetate displays chemopreventive activity, inhibiting development of azoxymethane-induced colon carcinogenesis. In vivo, this compound upregulates Nrf2 and induces expression of glutathione and NADPH quinone oxidoreductase 1. 1’-(S)-1’-Acetoxychavicol acetate also increases caspase-3 activity, inducing apoptosis and cell death in cellular models of glioblastoma and oral carcinoma.

Product Info

Cas No.

52946-22-2

Purity

≥98%

Formula

C13H14O4

Formula Wt.

234.25

Chemical Name

[4-[(1S)-1-acetyloxyprop-2-enyl]phenyl] acetate

IUPAC Name

[4-[(1S)-1-acetyloxyprop-2-enyl]phenyl] acetate

Synonym

Galangal acetate,(-); Galangal acetate,(S);

Solubility

Soluble in DMSO (20 mg/mL), ethanol (20 mg/mL), DMF (14 mg/mL). Insoluble in water (racemizes in the presence of moisture)

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

Info Sheet

A0917 Info Sheet PDF

References

Williams M, Tietzel I, Quick QA. 1'-Acetoxychavicol acetate promotes caspase 3-activated glioblastoma cell death by overcoming enhanced cytokine expression. Oncol Lett. 2013 Jun;5(6):1968-1972. PMID: 23833677.

Ohnishi R, Matsui-Yuasa I, Deguchi Y, et al. 1'-acetoxychavicol acetate inhibits adipogenesis in 3T3-L1 adipocytes and in high fat-fed rats. Am J Chin Med. 2012;40(6):1189-204. PMID: 23227791.

In LL, Arshad NM, Ibrahim H, et al. 1'-Acetoxychavicol acetate inhibits growth of human oral carcinoma xenograft in mice and potentiates cisplatin effect via proinflammatory microenvironment alterations. BMC Complement Altern Med. 2012 Oct 9;12:179. PMID: 23043547.

Yaku K, Matsui-Yuasa I, Azuma H, et al. 1'-Acetoxychavicol acetate enhances the phase II enzyme activities via the increase in intranuclear Nrf2 level and cytosolic p21 level. Am J Chin Med. 2011;39(4):789-802. PMID: 21721157.

Kaur A, Singh R, Dey CS, et al. Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd. Indian J Exp Biol. 2010 Mar;48(3):314-7. PMID: 21046987.

Narukawa M, Koizumi K, Iwasaki Y, et al. Galangal pungent component, 1'-acetoxychavicol acetate, activates TRPA1. Biosci Biotechnol Biochem. 2010;74(8):1694-6. PMID: 20699565

Latha C, Shriram VD, Jahagirdar SS, et al. Antiplasmid activity of 1'-acetoxychavicol acetate from Alpinia galanga against multi-drug resistant bacteria. J Ethnopharmacol. 2009 Jun 25;123(3):522-5. PMID: 19501283.

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