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MedKoo Cat#: 529106 | Name: Antroquinonol

Description:

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

Antroquinonol is potentially for the treatment of non-small cell lung cancer.

Chemical Structure

Antroquinonol
Antroquinonol
CAS#1010081-09-0

Theoretical Analysis

MedKoo Cat#: 529106

Name: Antroquinonol

CAS#: 1010081-09-0

Chemical Formula: C24H38O4

Exact Mass: 390.2700

Molecular Weight: 390.56

Elemental Analysis: C, 73.81; H, 9.81; O, 16.39

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Antroquinonol A; Antroquinonol;
IUPAC/Chemical Name
(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)cyclohex-2-en-1-one
InChi Key
LJTSIMVOOOLKOL-FNRDIUJOSA-N
InChi Code
InChI=1S/C24H38O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-20-19(5)21(25)23(27-6)24(28-7)22(20)26/h10,12,14,19-20,22,26H,8-9,11,13,15H2,1-7H3/b17-12+,18-14+/t19-,20-,22-/m1/s1
SMILES Code
O=C1C(OC)=C(OC)[C@H](O)[C@H](C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)[C@H]1C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 390.56 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
1: Hu YD, Lu RQ, Liao XR, Zhang BB, Xu GR. Stimulating the biosynthesis of antroquinonol by addition of effectors and soybean oil in submerged fermentation of Antrodia camphorata. Biotechnol Appl Biochem. 2016 May;63(3):398-406. doi: 10.1002/bab.1387. PubMed PMID: 25906825. 2: Thiyagarajan V, Tsai MJ, Weng CF. Antroquinonol Targets FAK-Signaling Pathway Suppressed Cell Migration, Invasion, and Tumor Growth of C6 Glioma. PLoS One. 2015 Oct 30;10(10):e0141285. doi: 10.1371/journal.pone.0141285. PubMed PMID: 26517117; PubMed Central PMCID: PMC4627804. 3: Hsu CY, Sulake RS, Huang PK, Shih HY, Sie HW, Lai YK, Chen C, Weng CF. Synthetic (+)-antroquinonol exhibits dual actions against insulin resistance by triggering AMP kinase and inhibiting dipeptidyl peptidase IV activities. Br J Pharmacol. 2015 Jan;172(1):38-49. doi: 10.1111/bph.12828. PubMed PMID: 24977411; PubMed Central PMCID: PMC4280966. 4: Xia Y, Zhou X, Wang G, Zhang B, Xu G, Ai L. Induction of antroquinonol production by addition of hydrogen peroxide in the fermentation of Antrodia camphorata S-29. J Sci Food Agric. 2017 Jan;97(2):595-599. doi: 10.1002/jsfa.7770. PubMed PMID: 27098319. 5: Ho CL, Wang JL, Lee CC, Cheng HY, Wen WC, Cheng HH, Chen MC. Antroquinonol blocks Ras and Rho signaling via the inhibition of protein isoprenyltransferase activity in cancer cells. Biomed Pharmacother. 2014 Oct;68(8):1007-14. doi: 10.1016/j.biopha.2014.09.008. PubMed PMID: 25312820. 6: Wang SC, Lee TH, Hsu CH, Chang YJ, Chang MS, Wang YC, Ho YS, Wen WC, Lin RK. Antroquinonol D, isolated from Antrodia camphorata, with DNA demethylation and anticancer potential. J Agric Food Chem. 2014 Jun 18;62(24):5625-35. doi: 10.1021/jf4056924. PubMed PMID: 24784321. 7: Lee YC, Ho CL, Kao WY, Chen YM. A phase I multicenter study of antroquinonol in patients with metastatic non-small-cell lung cancer who have received at least two prior systemic treatment regimens, including one platinum-based chemotherapy regimen. Mol Clin Oncol. 2015 Nov;3(6):1375-1380. PubMed PMID: 26807250; PubMed Central PMCID: PMC4665158. 8: Chang WH, Chen MC, Cheng IH. Antroquinonol Lowers Brain Amyloid-β Levels and Improves Spatial Learning and Memory in a Transgenic Mouse Model of Alzheimer's Disease. Sci Rep. 2015 Oct 15;5:15067. doi: 10.1038/srep15067. PubMed PMID: 26469245; PubMed Central PMCID: PMC4606808. 9: Yu CC, Chiang PC, Lu PH, Kuo MT, Wen WC, Chen P, Guh JH. Antroquinonol, a natural ubiquinone derivative, induces a cross talk between apoptosis, autophagy and senescence in human pancreatic carcinoma cells. J Nutr Biochem. 2012 Aug;23(8):900-7. doi: 10.1016/j.jnutbio.2011.04.015. PubMed PMID: 21840189. 10: Kumar VB, Yuan TC, Liou JW, Yang CJ, Sung PJ, Weng CF. Antroquinonol inhibits NSCLC proliferation by altering PI3K/mTOR proteins and miRNA expression profiles. Mutat Res. 2011 Feb 10;707(1-2):42-52. doi: 10.1016/j.mrfmmm.2010.12.009. PubMed PMID: 21185843. 11: Kumar KJ, Chu FH, Hsieh HW, Liao JW, Li WH, Lin JC, Shaw JF, Wang SY. Antroquinonol from ethanolic extract of mycelium of Antrodia cinnamomea protects hepatic cells from ethanol-induced oxidative stress through Nrf-2 activation. J Ethnopharmacol. 2011 Jun 14;136(1):168-77. doi: 10.1016/j.jep.2011.04.030. PubMed PMID: 21540101. 12: Lee WT, Lee TH, Cheng CH, Chen KC, Chen YC, Lin CW. Antroquinonol from Antrodia Camphorata suppresses breast tumor migration/invasion through inhibiting ERK-AP-1- and AKT-NF-κB-dependent MMP-9 and epithelial-mesenchymal transition expressions. Food Chem Toxicol. 2015 Apr;78:33-41. doi: 10.1016/j.fct.2015.01.012. PubMed PMID: 25656647. 13: Sulake RS, Chen C. Total synthesis of (+)-antroquinonol and (+)-antroquinonol D. Org Lett. 2015 Mar 6;17(5):1138-41. doi: 10.1021/acs.orglett.5b00046. PubMed PMID: 25679542. 14: Tsai PY, Ka SM, Chang JM, Lai JH, Dai MS, Jheng HL, Kuo MT, Chen P, Chen A. Antroquinonol differentially modulates T cell activity and reduces interleukin-18 production, but enhances Nrf2 activation, in murine accelerated severe lupus nephritis. Arthritis Rheum. 2012 Jan;64(1):232-42. doi: 10.1002/art.33328. PubMed PMID: 21905011. 15: Chiang PC, Lin SC, Pan SL, Kuo CH, Tsai IL, Kuo MT, Wen WC, Chen P, Guh JH. Antroquinonol displays anticancer potential against human hepatocellular carcinoma cells: a crucial role of AMPK and mTOR pathways. Biochem Pharmacol. 2010 Jan 15;79(2):162-71. doi: 10.1016/j.bcp.2009.08.022. PubMed PMID: 19723512. 16: Sulake RS, Lin HH, Hsu CY, Weng CF, Chen C. Synthesis of (+)-Antroquinonol: An Antihyperglycemic Agent. J Org Chem. 2015 Jun 19;80(12):6044-51. doi: 10.1021/acs.joc.5b00345. PubMed PMID: 26039178. 17: Yang SM, Ka SM, Hua KF, Wu TH, Chuang YP, Lin YW, Yang FL, Wu SH, Yang SS, Lin SH, Chang JM, Chen A. Antroquinonol mitigates an accelerated and progressive IgA nephropathy model in mice by activating the Nrf2 pathway and inhibiting T cells and NLRP3 inflammasome. Free Radic Biol Med. 2013 Aug;61:285-97. doi: 10.1016/j.freeradbiomed.2013.03.024. PubMed PMID: 23567192. 18: Hsu CS, Chou HH, Fang JM. A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone. Org Biomol Chem. 2015 May 21;13(19):5510-9. doi: 10.1039/c5ob00411j. PubMed PMID: 25875221. 19: Chen CK, Kang JJ, Wen WC, Chiang HF, Lee SS. Metabolites of antroquinonol found in rat urine following oral administration. J Nat Prod. 2014 Apr 25;77(4):1061-4. doi: 10.1021/np400670a. PubMed PMID: 24593224. 20: Sulake RS, Jiang YF, Lin HH, Chen C. Total synthesis of (±)-antroquinonol d. J Org Chem. 2014 Nov 21;79(22):10820-8. doi: 10.1021/jo501735z. PubMed PMID: 25375772.