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D,L-1’-Acetoxychavicol acetate

D,L-1’-Acetoxychavicol acetate

Product ID A0817
Cas No. 52946-22-2, 53890-21-4
Purity ≥98%
Product Unit SizeCostQuantityStock
25 mg $105.00 In stock
100 mg $388.40 In stock
250 mg $709.20 In stock
Bulk Quote

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  • Product Info
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  • Downloads
  • References
  • Description
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Description

1’-Acetoxychavicol acetate (ACA) was originally found in Alpinia galanga; it exhibits anti-obesity, immunomodulatory, anti-inflammatory, anti-asthma, anti-allergic, antibiotic, antiviral, anti-parasitic, anti-angiogenic, anti-metastatic, anticancer chemotherapeutic, and chemopreventive activities. ACA activates transient receptor potential A1 (TRPA1) channels and inhibits xanthine oxidase. ACA inhibits proliferation of Staphylococcus and Leishmania and suppresses replication of the influenza virus by inhibiting CRM1. In animal models fed high-fat diets, ACA limits activity of glucose-6-phosphate dehydrogenase, suppresses lipid accumulation, increases activation of AMPK, and decreases fat mass and body weight. In animal models of OVA-induced asthma, ACA suppresses eosinophil infiltration, decreases levels of IgE, IL-4, IL-13, IL-12α, and IFN-γ, and prevents airway remodeling. In vitro, this compound increases levels of glutathione-S-transferase, NQO1, glutathione, Nrf2, and p21. Additionally, ACA inhibits VEGF-induced cellular proliferation, migration, adhesion, and tube formation in various in vitro and in vivo models. ACA also decreases NF-κB activation and invasiveness in cellular models. In vivo, this compound prevents skin tumor carcinogenesis. In cellular and animal models of oral squamous cell carcinoma, ACA inhibits cellular proliferation and decreases tumor volume. In glioblastoma cells, this compound decreases levels of IL-6 and IL-1α, inhibits cellular proliferation and migration, and induces apoptosis.

Product Info

Cas No.

52946-22-2, 53890-21-4

Purity

≥98%

Formula

C13H14O4

Formula Wt.

234.25

Chemical Name

D,L-1’-Acetoxychavicol acetate

IUPAC Name

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

Synonym

4-(Acetyloxy)-alpha-ethenylbenzenemethanol, CCRIS 7708; 1′-R,S-Acetoxychavicol Acetate; 1’-R,S-ACA. Galangal acetate, (RS)-; Galangal acetate, (+/-)-

Solubility

Soluble in DMSO (20 mg/mL), ethanol (20 mg/mL), DMF (14 mg/mL).

Appearance

White Crystal Powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

A0817 MSDS PDF

Info Sheet

A0817 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.

Seo JW, Cho SC, Park SJ, et al. 1'-Acetoxychavicol acetate isolated from Alpinia galanga ameliorates ovalbumin-induced asthma in mice. PLoS One. 2013;8(2):e56447. PMID: 23451048.

Aziz AN, Ibrahim H, Rosmy Syamsir D, et al. Antimicrobial compounds from Alpinia conchigera. J Ethnopharmacol. 2013 Feb 13;145(3):798-802. PMID: 23266278.

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.

Batra V, Syed Z, Gill JN, et al. Effects of the tropical ginger compound,1'-acetoxychavicol acetate, against tumor promotion in K5.Stat3C transgenic mice. J Exp Clin Cancer Res. 2012 Jun 15;31:57. PMID: 22704648.

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.

Pang X, Zhang L, Lai L, et al. 1'-Acetoxychavicol acetate suppresses angiogenesis-mediated human prostate tumor growth by targeting VEGF-mediated Src-FAK-Rho GTPase-signaling pathway. Carcinogenesis. 2011 Jun;32(6):904-12. PMID: 21427164.

Watanabe K, Takatsuki H, Sonoda M, et al. Anti-influenza viral effects of novel nuclear export inhibitors from Valerianae Radix and Alpinia galanga. Drug Discov Ther. 2011 Feb;5(1):26-31. PMID: 22466093.

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.

Ichikawa H, Takada Y, Murakami A, et al. Identification of a novel blocker of I kappa B alpha kinase that enhances cellular apoptosis and inhibits cellular invasion through suppression of NF-kappa B-regulated gene products. J Immunol. 2005 Jun 1;174(11):7383-92. PMID: 15905586.

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