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MedKoo Cat#: 466171 | Name: 4-Aaqb

Description:

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

4-Aaqb, also known as OB-318, is a natural inhibitor of the autophagy pathway, enhancing immune function, suppressing MAPK and NFκB, showing anti-inflammatory, hypoglycemic, vasorelaxative, and antiproliferative activities.

Chemical Structure

4-Aaqb
4-Aaqb
CAS#1187652-02-3

Theoretical Analysis

MedKoo Cat#: 466171

Name: 4-Aaqb

CAS#: 1187652-02-3

Chemical Formula: C26H38O7

Exact Mass: 462.2618

Molecular Weight: 462.58

Elemental Analysis: C, 67.51; H, 8.28; O, 24.21

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 #
No Data
Synonym
4-Aaqb; 4Aaqb; 4 Aaqb; 4-Acetylantroquinonol B; 4 Acetylantroquinonol B; OB-318; OB318; OB 318;
IUPAC/Chemical Name
(1R,5R,6R)-6-((2E,6E)-3,7-dimethyl-8-((2R,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)octa-2,6-dien-1-yl)-2,3-dimethoxy-5-methyl-4-oxocyclohex-2-en-1-yl acetate
InChi Key
XXAVUEUAHANHQA-ZXOJLNOSSA-N
InChi Code
InChI=1S/C26H38O7/c1-15(9-8-10-16(2)13-20-14-17(3)26(29)33-20)11-12-21-18(4)22(28)24(30-6)25(31-7)23(21)32-19(5)27/h10-11,17-18,20-21,23H,8-9,12-14H2,1-7H3/b15-11+,16-10+/t17-,18+,20-,21+,23+/m0/s1
SMILES Code
CC(O[C@H]1C(OC)=C(OC)C([C@H](C)[C@H]1C/C=C(C)/CC/C=C(C)/C[C@@H](C[C@@H]2C)OC2=O)=O)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 462.58 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: Wu CZ, Chu YC, Lai SW, Hsieh MS, Yadav VK, Fong IH, Deng L, Huang CC, Tzeng YM, Yeh CT, Chen JS. Urokinase plasminogen activator induces epithelial- mesenchymal and metastasis of pancreatic cancer through plasmin/MMP14/TGF-β axis, which is inhibited by 4-acetyl-antroquinonol B treatment. Phytomedicine. 2022 Jun;100:154062. doi: 10.1016/j.phymed.2022.154062. Epub 2022 Mar 16. PMID: 35366491. 2: Liu H, Xing H, Jin Y, Liu J, Tzeng YM, Deng L, Wang F. Application of Multiple Strategies to Improve the Production of the Potential Cancer Drug 4-Acetylantroquinonol B (4-AAQB) by the Rare Fungus Antrodia cinnamomea. Appl Biochem Biotechnol. 2022 Mar 8. doi: 10.1007/s12010-022-03811-0. Epub ahead of print. PMID: 35257317. 3: Chen YY, Chen SY, Li TJ, Lin TW, Chen CC, Yen GC. 4-Acetylantroquinonol B enhances cell death and inhibits autophagy by downregulating the PI3K/Akt/MDR1 pathway in gemcitabine-resistant pancreatic cancer cells. Oncol Lett. 2022 Apr;23(4):128. doi: 10.3892/ol.2022.13248. Epub 2022 Feb 18. PMID: 35251348; PMCID: PMC8895450. 4: Chu YC, Tsai TY, Yadav VK, Deng L, Huang CC, Tzeng YM, Yeh CT, Chen MY. 4-Acetyl-Antroquinonol B Improves the Sensitization of Cetuximab on Both Kras Mutant and Wild Type Colorectal Cancer by Modulating the Expression of Ras/Raf/miR-193a-3p Signaling Axis. Int J Mol Sci. 2021 Jul 14;22(14):7508. doi: 10.3390/ijms22147508. PMID: 34299137; PMCID: PMC8307961. 5: Yen IC, Tu QW, Chang TC, Lin PH, Li YF, Lee SY. 4-Acetylantroquinonol B ameliorates nonalcoholic steatohepatitis by suppression of ER stress and NLRP3 inflammasome activation. Biomed Pharmacother. 2021 Jun;138:111504. doi: 10.1016/j.biopha.2021.111504. Epub 2021 Mar 24. PMID: 33773468. 6: Satriyo PB, Su CM, Ong JR, Huang WC, Fong IH, Lin CC, Aryandono T, Haryana SM, Deng L, Huang CC, Tzeng YM, Chao TY, Liu HW, Yeh CT. 4-Acetylantroquinonol B induced DNA damage response signaling and apoptosis via suppressing CDK2/CDK4 expression in triple negative breast cancer cells. Toxicol Appl Pharmacol. 2021 Jul 1;422:115493. doi: 10.1016/j.taap.2021.115493. Epub 2021 Mar 13. PMID: 33727089. 7: Lin TC, Germagian A, Liu Z. The NF-[Formula: see text]B Signaling and Wnt/[Formula: see text]-catenin Signaling in MCF-7 Breast Cancer Cells in Response to Bioactive Components from Mushroom Antrodia Camphorata. Am J Chin Med. 2021;49(1):199-215. doi: 10.1142/S0192415X21500117. Epub 2020 Dec 26. PMID: 33371814. 8: Wu CH, Ou CH, Yen IC, Lee SY. 4-Acetylantroquinonol B Inhibits Osteoclastogenesis by Inhibiting the Autophagy Pathway in a Simulated Microgravity Model. Int J Mol Sci. 2020 Sep 22;21(18):6971. doi: 10.3390/ijms21186971. PMID: 32971944; PMCID: PMC7555662. 9: Chou KC, Wu HL, Lin PY, Yang SH, Chang TL, Sheu F, Chen KH, Chiang BH. 4-Hydroxybenzoic acid serves as an endogenous ring precursor for antroquinonol biosynthesis in Antrodia cinnamomea. Phytochemistry. 2019 May;161:97-106. doi: 10.1016/j.phytochem.2019.02.011. Epub 2019 Feb 26. PMID: 30822625. 10: Liu HW, Su YK, Bamodu OA, Hueng DY, Lee WH, Huang CC, Deng L, Hsiao M, Chien MH, Yeh CT, Lin CM. The Disruption of the β-Catenin/TCF-1/STAT3 Signaling Axis by 4-Acetylantroquinonol B Inhibits the Tumorigenesis and Cancer Stem-Cell-Like Properties of Glioblastoma Cells, In Vitro and In Vivo. Cancers (Basel). 2018 Dec 5;10(12):491. doi: 10.3390/cancers10120491. PMID: 30563094; PMCID: PMC6315804. 11: Li TY, Chiang BH. 4-Acetylantroquinonol B from antrodia cinnamomea enhances immune function of dendritic cells against liver cancer stem cells. Biomed Pharmacother. 2019 Jan;109:2262-2269. doi: 10.1016/j.biopha.2018.11.101. Epub 2018 Nov 28. PMID: 30551483. 12: Bamodu OA, Yang CK, Cheng WH, Tzeng DTW, Kuo KT, Huang CC, Deng L, Hsiao M, Lee WH, Yeh CT. 4-Acetyl-Antroquinonol B Suppresses SOD2-Enhanced Cancer Stem Cell-Like Phenotypes and Chemoresistance of Colorectal Cancer Cells by Inducing hsa-miR-324 re-Expression. Cancers (Basel). 2018 Aug 10;10(8):269. doi: 10.3390/cancers10080269. PMID: 30103475; PMCID: PMC6116152. 13: Liu M, Bamodu OA, Huang WC, Zucha MA, Lin YK, Wu ATH, Huang CC, Lee WH, Yuan CC, Hsiao M, Deng L, Tzeng YM, Yeh CT. 4-Acetylantroquinonol B suppresses autophagic flux and improves cisplatin sensitivity in highly aggressive epithelial cancer through the PI3K/Akt/mTOR/p70S6K signaling pathway. Toxicol Appl Pharmacol. 2017 Jun 15;325:48-60. doi: 10.1016/j.taap.2017.04.003. Epub 2017 Apr 10. PMID: 28408137. 14: Chou KC, Yang SH, Wu HL, Lin PY, Chang TL, Sheu F, Chen KH, Chiang BH. Biosynthesis of Antroquinonol and 4-Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea. J Agric Food Chem. 2017 Jan 11;65(1):74-86. doi: 10.1021/acs.jafc.6b04346. Epub 2016 Dec 21. PMID: 28001060. 15: Chang TC, Yeh CT, Adebayo BO, Lin YC, Deng L, Rao YK, Huang CC, Lee WH, Wu AT, Hsiao M, Wu CH, Wang LS, Tzeng YM. 4-Acetylantroquinonol B inhibits colorectal cancer tumorigenesis and suppresses cancer stem-like phenotype. Toxicol Appl Pharmacol. 2015 Oct 15;288(2):258-68. doi: 10.1016/j.taap.2015.07.025. Epub 2015 Jul 30. PMID: 26235807.