Yakuchinone A
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MedKoo CAT#: 341100

CAS#: 78954-23-1

Description: Yakuchinone-A is a natural product isolated from Alpinia oxyphylla Miquel (Zingiberaceae). Yakuchinone-A has strong inhibitory effects on the synthesis of prostaglandins and leukotrienes in vitro. Yakuchinone A inhibits the expression of cyclooxygenase-2 (COX-2) and of inducible nitric oxide synthase (iNOS) as well as the expression of tumor necrosis factor (TNF)-alpha mRNA in mouse skin treated with the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).


Chemical Structure

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Yakuchinone A
CAS# 78954-23-1

Theoretical Analysis

MedKoo Cat#: 341100
Name: Yakuchinone A
CAS#: 78954-23-1
Chemical Formula: C20H24O3
Exact Mass: 312.1725
Molecular Weight: 312.409
Elemental Analysis: C, 76.89; H, 7.74; O, 15.36

Price and Availability

Size Price Availability Quantity
200.0mg USD 250.0 2 Weeks
500.0mg USD 550.0 2 Weeks
1.0g USD 950.0 2 Weeks
2.0g USD 1650.0 2 Weeks
5.0g USD 3350.0 2 Weeks
10.0g USD 5950.0 2 Weeks
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Synonym: Yakuchinone-A

IUPAC/Chemical Name: 3-Heptanone, 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-

InChi Key: TXELARZTKDBEKS-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3

SMILES Code: O=C(CCCCC1=CC=CC=C1)CCC2=CC=C(O)C(OC)=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 312.409 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zhang Q, Cui C, Chen CQ, Hu XL, Liu YH, Fan YH, Meng WH, Zhao QC. Anti-proliferative and pro-apoptotic activities of Alpinia oxyphylla on HepG2 cells through ROS-mediated signaling pathway. J Ethnopharmacol. 2015 Jul 1;169:99-108. doi: 10.1016/j.jep.2015.03.073. Epub 2015 Apr 16. PubMed PMID: 25891473.

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5: Chen F, Li HL, Tan YF, Guan WW, Li YH, Zhang JQ. Validated method to measure yakuchinone A in plasma by LC-MS/MS and its application to a pharmacokinetic study in rats. Chem Cent J. 2014 Jan 14;8(1):2. doi: 10.1186/1752-153X-8-2. PubMed PMID: 24422995; PubMed Central PMCID: PMC3896807.

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13: Chun KS, Kang JY, Kim OH, Kang H, Surh YJ. Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol. 2002;21(2):131-9. PubMed PMID: 12086399.

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20: Flynn DL, Rafferty MF, Boctor AM. Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally-occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones. Prostaglandins Leukot Med. 1986 Jun;22(3):357-60. PubMed PMID: 3460103.