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MedKoo Cat#: 341100 | Name: Yakuchinone A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Yakuchinone A
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: 312.41

Elemental Analysis: C, 76.89; H, 7.74; O, 15.36

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,650.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 5,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Yakuchinone-A; Yakuchinone A; YakuchinoneA
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
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).
In vitro activity:
Antioxidant and antitumor characteristics of yakuchinone A in skin cancer cells as well as novel mechanisms for the inhibition of adipocyte differentiation, cestocidal activities against Hymenolepis nana adults, and nematocidal activities against Anisakis simplex larvae were investigated in this study. Yakuchinone A presents the ability of the removal of DPPH·and ABTS+ free radicals and inhibition of lipid peroxidation. Yakuchinone A suppresses intracellular lipid accumulation during adipocyte differentiation in 3 T3-L1 cells and the expressions of leptin and peroxisome proliferator-activated receptor γ (PPARγ). Yakuchinone A induces apoptosis and inhibits cell proliferation in skin cancer cells. The inhibition of cell growth by yakuchinone A is more significant for non-melanoma skin cancer (NMSC) cells than for melanoma (A375 and B16) and noncancerous (HaCaT and BNLCL2) cells. Treatment BCC cells with yakuchinone A shows down-regulation of Bcl-2, up-regulation of Bax, and an increase in cleavage poly (ADP-ribose) polymerase (PARP). This suggests that yakuchinone A induces BCC cells apoptosis through the Bcl-2-mediated signaling pathway. The anthelmintic activities of yakuchinone A for A. simplex are better than for H. nana. Reference: BMC Complement Altern Med. 2013 Sep 26;13:237. https://pubmed.ncbi.nlm.nih.gov/24070160/
In vivo activity:
In the present work, the effects of yakuchinone A and yakuchinone B, phenolic diarylheptanoids derived from A. oxyphylla, on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation and epidermal ornithine decarboxylase (ODC) activity as well as on skin tumor promotion in female ICR mice were assessed. Thus, topical application of 2 or 6 micromol of the diarylheptanoids prior to each topical dose of TPA significantly ameliorated 7,12-dimethylbenz[a]anthracene-initiated mouse skin tumor formation. In parallel with suppression of tumor promotion, topically applied yakuchinone A and B markedly inhibited TPA-induced epidermal ODC activity and ODC mRNA expression. In another experiment, yakuchinone A and B reduced production of tumor necrosis factor-alpha in TPA-stimulated mouse skin. Furthermore, both compounds inhibited the TPA-induced expression of cyclooxygenase-2 at both transcriptional and translational levels. These findings indicate that pungent diarylheptanoids from A. oxyphylla Miquel have an antitumor promotional activity that might be related to their anti-inflammatory properties. Reference: Oncol Res. 2002;13(1):37-45. https://pubmed.ncbi.nlm.nih.gov/12201673/
Solvent mg/mL mM
Solubility
DMSO 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 312.41 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
Formulation protocol:
1. Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PMID: 24070160; PMCID: PMC3879407. 2. Huang KK, Lin MN, Hsu YL, Lu IH, Pan IH, Yang JL. Alpinia oxyphylla Fruit Extract Ameliorates Experimental Autoimmune Encephalomyelitis through the Regulation of Th1/Th17 Cells. Evid Based Complement Alternat Med. 2019 Mar 14;2019:6797030. doi: 10.1155/2019/6797030. PMID: 31001353; PMCID: PMC6437745. 3. 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. PMID: 12086399. 4. Chun KS, Park KK, Lee J, Kang M, Surh YJ. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol Res. 2002;13(1):37-45. doi: 10.3727/096504002108747944. PMID: 12201673.
In vitro protocol:
1. Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PMID: 24070160; PMCID: PMC3879407. 2. Huang KK, Lin MN, Hsu YL, Lu IH, Pan IH, Yang JL. Alpinia oxyphylla Fruit Extract Ameliorates Experimental Autoimmune Encephalomyelitis through the Regulation of Th1/Th17 Cells. Evid Based Complement Alternat Med. 2019 Mar 14;2019:6797030. doi: 10.1155/2019/6797030. PMID: 31001353; PMCID: PMC6437745.
In vivo protocol:
1. 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. PMID: 12086399. 2. Chun KS, Park KK, Lee J, Kang M, Surh YJ. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol Res. 2002;13(1):37-45. doi: 10.3727/096504002108747944. PMID: 12201673.
1: Cruz-Cortés C, Fernández-de Gortari E, Aguayo-Ortiz R, Šeflová J, Ard A, Clasby M, Anumonwo J, Michel Espinoza-Fonseca L. Machine Learning-Driven Discovery of Structurally Related Natural Products as Activators of the Cardiac Calcium Pump SERCA2a. ChemMedChem. 2025 Jan 23:e202400913. doi: 10.1002/cmdc.202400913. Epub ahead of print. PMID: 39853697. 2: Huang Y, Ren X, Li Y, Zhang J, Wei N, Li H, Tan Y. Comparisons of pharmacokinetics and tissue distribution of six major bioactive components of the herbal pair Alpinia officinarum-Cyperus rotundus in normal and primary dysmenorrhea rats. J Pharm Biomed Anal. 2024 Sep 15;248:116316. doi: 10.1016/j.jpba.2024.116316. Epub 2024 Jun 19. PMID: 38941920. 3: Kim SH, Na C, Yun CY, Kim JG, Baek ST, An HJ, Lee JD, Lee SW, Jung JK, Hwang BY, Han SB, Kim Y. Targeting phosphorylation circuits on CREB and CRTCs as the strategy to prevent acquired skin hyperpigmentation. Int J Biol Sci. 2024 Jan 1;20(1):312-330. doi: 10.7150/ijbs.86536. PMID: 38164184; PMCID: PMC10750286. 4: Han C, Bao H. Therapeutic effects and mechanisms of Inonotus hispidus extract and active monomer compounds in a rat mammary gland hyperplasia model. J Ethnopharmacol. 2024 Jan 30;319(Pt 2):117274. doi: 10.1016/j.jep.2023.117274. Epub 2023 Oct 4. PMID: 37797875. 5: Zeng P, Liu YC, Wang XM, Ye CY, Sun YW, Su HF, Qiu SW, Li YN, Wang Y, Wang YC, Ma J, Li M, Tian Q. Targets and mechanisms of Alpinia oxyphylla Miquel fruits in treating neurodegenerative dementia. Front Aging Neurosci. 2022 Nov 30;14:1013891. doi: 10.3389/fnagi.2022.1013891. PMID: 36533181; PMCID: PMC9749063. 6: Park CL, Kim JH, Jeon JS, Lee JH, Zhang K, Guo S, Lee DH, Gao EM, Son RH, Kim YM, Park GH, Kim CY. Protective Effect of Alpinia oxyphylla Fruit against tert-Butyl Hydroperoxide-Induced Toxicity in HepG2 Cells via Nrf2 Activation and Free Radical Scavenging and Its Active Molecules. Antioxidants (Basel). 2022 May 23;11(5):1032. doi: 10.3390/antiox11051032. PMID: 35624896; PMCID: PMC9137508. 7: Huo C, Han F, Xiao Y, Kim HJ, Lee IS. Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites. Int J Mol Sci. 2022 Apr 3;23(7):3992. doi: 10.3390/ijms23073992. PMID: 35409351; PMCID: PMC9000044. 8: Ullah MA, Johora FT, Sarkar B, Araf Y, Rahman MH. Curcumin analogs as the inhibitors of TLR4 pathway in inflammation and their drug like potentialities: a computer-based study. J Recept Signal Transduct Res. 2020 Aug;40(4):324-338. doi: 10.1080/10799893.2020.1742741. Epub 2020 Mar 30. PMID: 32223496. 9: Huang KK, Lin MN, Hsu YL, Lu IH, Pan IH, Yang JL. Alpinia oxyphylla Fruit Extract Ameliorates Experimental Autoimmune Encephalomyelitis through the Regulation of Th1/Th17 Cells. Evid Based Complement Alternat Med. 2019 Mar 14;2019:6797030. doi: 10.1155/2019/6797030. PMID: 31001353; PMCID: PMC6437745. 10: Tasneem S, Liu B, Li B, Choudhary MI, Wang W. Molecular pharmacology of inflammation: Medicinal plants as anti-inflammatory agents. Pharmacol Res. 2019 Jan;139:126-140. doi: 10.1016/j.phrs.2018.11.001. Epub 2018 Nov 3. PMID: 30395947. 11: Wen Q, Li HL, Chen F, Gong JW, Guan WW, Fu NG, Tan YF. Development and validation of an LC-MS/MS method for the determination of DPHB in rat plasma and its application in pharmacokinetic studies. Biomed Chromatogr. 2018 Dec;32(12):e4373. doi: 10.1002/bmc.4373. Epub 2018 Sep 26. PMID: 30133708. 12: Zhang Q, Zheng Y, Hu X, Hu X, Lv W, Lv D, Chen J, Wu M, Song Q, Shentu J. Ethnopharmacological uses, phytochemistry, biological activities, and therapeutic applications of Alpinia oxyphylla Miquel: A review. J Ethnopharmacol. 2018 Oct 5;224:149-168. doi: 10.1016/j.jep.2018.05.002. Epub 2018 May 5. PMID: 29738847. 13: 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. PMID: 25891473. 14: Yuan Y, Tan YF, Xu P, Li H, Li YH, Chen WY, Zhang JQ, Chen F, Huang GJ. Izalpinin from fruits of Alpinia oxyphylla with antagonistic activity against the rat bladder contractility. Afr J Tradit Complement Altern Med. 2014 Jun 4;11(4):120-5. doi: 10.4314/ajtcam.v11i4.18. PMID: 25392590; PMCID: PMC4202406. 15: Chen F, Li HL, Tan YF, Li YH, Lai WY, Guan WW, Zhang JQ, Zhao YS, Qin ZM. Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring. J Pharm Biomed Anal. 2014 Aug;97:166-77. doi: 10.1016/j.jpba.2014.04.037. Epub 2014 May 10. PMID: 24879483. 16: Chen F, Li HL, Tan YF, Guan WW, Zhang JQ, Li YH, Zhao YS, Qin ZM. Different accumulation profiles of multiple components between pericarp and seed of Alpinia oxyphylla capsular fruit as determined by UFLC-MS/MS. Molecules. 2014 Apr 10;19(4):4510-23. doi: 10.3390/molecules19044510. PMID: 24727421; PMCID: PMC6271690. 17: 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. PMID: 24422995; PMCID: PMC3896807. 18: Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PMID: 24070160; PMCID: PMC3879407. 19: Chen F, Li HL, Li YH, Tan YF, Zhang JQ. Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry. Chem Cent J. 2013 Jul 30;7(1):131. doi: 10.1186/1752-153X-7-131. PMID: 23899222; PMCID: PMC3733971. 20: Bian QY, Wang SY, Xu LJ, Chan CO, Mok DK, Chen SB. Two new antioxidant diarylheptanoids from the fruits of Alpinia oxyphylla. J Asian Nat Prod Res. 2013;15(10):1094-9. doi: 10.1080/10286020.2013.816297. Epub 2013 Jul 22. PMID: 23869536.

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