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MedKoo Cat#: 465303 | Name: Triptophenolide
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Description:

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

Triptophenolide is a diterpenoid that has been found in T. wilfordii and has antiandrogenic activity. It is an antagonist of wild-type and mutant androgen receptors (ARs; IC50s = 260, 388, 480, and 437 nM for wild-type, ART877A, ARF876L, and ARW741C/T877A, respectively, in transactivation assays). Triptophenolide (5 µM) inhibits the growth of, and reduces AR levels in, LNCaP prostate cancer cells.

Chemical Structure

Triptophenolide
Triptophenolide
CAS#74285-86-2

Theoretical Analysis

MedKoo Cat#: 465303

Name: Triptophenolide

CAS#: 74285-86-2

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
1mg USD 250.00 2 Weeks
5mg USD 580.00 2 Weeks
10mg USD 930.00 2 Weeks
25mg USD 1,600.00 2 Weeks
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Related CAS #
No Data
Synonym
Triptophenolide; Hypolide; (+)-Triptophenolide; (+) Triptophenolide;
IUPAC/Chemical Name
(3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[1,2-c]furan-1(3H)-one
InChi Key
KPXIBWGPZSPABK-FXAWDEMLSA-N
InChi Code
InChI=1S/C20H24O3/c1-11(2)12-4-6-16-14(18(12)21)5-7-17-15-10-23-19(22)13(15)8-9-20(16,17)3/h4,6,11,17,21H,5,7-10H2,1-3H3/t17-,20+/m0/s1
SMILES Code
C[C@]12[C@]([H])(C3=C(CC2)C(OC3)=O)CCC4=C(C(C(C)C)=CC=C41)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
Solvent mg/mL mM
Solubility
DMF 30.0 96.03
DMSO 30.0 96.03
DMSO:PBS (pH 7.2) (1:3) 0.3 0.80
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
1: Pu X, Ye Q. Triptophenolide Improves Rheumatoid Arthritis and Progression by Inducing Macrophage Toxicity. J Biochem Mol Toxicol. 2025 Jan;39(1):e70096. doi: 10.1002/jbt.70096. PMID: 39722460. 2: Bian XX, Ji XY, Tao XY, Xu LT, Ruan XY, Xie YR, Ji YP, Liu GQ, Zheng YX, Han F, Zhang XP, Zhan SY. [Comparison on pharmacokinetics of six active components of Tripterygium wilfordii Polyglycosides Tablets between normal rats and rat model of adjuvant arthritis]. Zhongguo Zhong Yao Za Zhi. 2024 Oct;49(20):5587-5597. Chinese. doi: 10.19540/j.cnki.cjcmm.20240711.201. PMID: 39701741. 3: Jiang M, Hou Q, Wu S, He X, Zhang T, Zhou R. Metabolic profiling of triptophenolide in rat plasma, urine, bile and faeces after intragastric administration. Nat Prod Res. 2024 Sep 3:1-5. doi: 10.1080/14786419.2024.2395496. Epub ahead of print. PMID: 39225372. 4: Huang Q, Tan C, Zheng C, Meng H, Wang Z, Lin GQ, Zhang W, Chen B, He QL. DCTPP1, a reliable Q-biomarker for comprehensive evaluation of the quality of tripterygium glycoside tablets based on chemical references. Phytomedicine. 2023 Oct;119:154972. doi: 10.1016/j.phymed.2023.154972. Epub 2023 Jul 23. PMID: 37531903. 5: Li M, Luo Q, Chen X, Qiu F, Tao Y, Sun X, Liu C. Screening of major hepatotoxic components of Tripterygium wilfordii based on hepatotoxic injury patterns. BMC Complement Med Ther. 2023 Jan 10;23(1):9. doi: 10.1186/s12906-023-03836-w. PMID: 36627617; PMCID: PMC9830834. 6: Song Y, Chen S, Wang X, Zhang R, Tu L, Hu T, Liu X, Zhang Y, Huang L, Gao W. A novel strategy to enhance terpenoids production using cambial meristematic cells of Tripterygium wilfordii Hook. f. Plant Methods. 2019 Nov 7;15:129. doi: 10.1186/s13007-019-0513-x. PMID: 31719835; PMCID: PMC6836502. 7: Wu XY, Zhang R, Ma Y, Meng LJ, Tu LC, Hu TY, Gao W. [Effect of GR24 on accumulation of diterpenoids in Tripterygium wilfordii suspension cells]. Zhongguo Zhong Yao Za Zhi. 2019 Aug;44(16):3582-3587. Chinese. doi: 10.19540/j.cnki.cjcmm.20190605.502. PMID: 31602926. 8: Ma B, Liu X, Lu Y, Ma X, Wu X, Wang X, Jia M, Su P, Tong Y, Guan H, Jiang Z, Gao J, Huang L, Gao W. A specific UDP-glucosyltransferase catalyzes the formation of triptophenolide glucoside from Tripterygium wilfordii Hook. f. Phytochemistry. 2019 Oct;166:112062. doi: 10.1016/j.phytochem.2019.112062. Epub 2019 Jul 9. PMID: 31299395. 9: Du X, He X, Huang Y, Fu B, Liang B, Lv C, Li Y, Gao X, Wang Y. Simultaneous determination of seven effective components of Tripterygium glycosides in human biological matrices by ultra performance liquid chromatography-triple quadrupole mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Apr 15;1113:1-13. doi: 10.1016/j.jchromb.2019.02.024. Epub 2019 Feb 25. PMID: 30877981. 10: Guo H, Wang Z, Xu L, Zhang H, Chang R, Chen A. Separation and simultaneous determination of seven bioactive components in Tripterygium wilfordii Hook. F. and Tripterygium preparations by micellar electrokinetic capillary chromatography. Electrophoresis. 2019 Feb;40(4):547-554. doi: 10.1002/elps.201800455. Epub 2018 Dec 12. PMID: 30511389. 11: Chen YL, Liu X, Qu XY, Yao YY, Li N, Liang XM, Zhang YY, Yang DJ, Zhang XM. [Studies on difference of chemical compositions in plant species of Tripterygium genus]. Zhongguo Zhong Yao Za Zhi. 2017 Jan;42(2):319-325. Chinese. doi: 10.19540/j.cnki.cjcmm.20161222.011. PMID: 28948738. 12: Xu H, Liu L, Fan X, Zhang G, Li Y, Jiang B. Identification of a diverse synthetic abietane diterpenoid library for anticancer activity. Bioorg Med Chem Lett. 2017 Feb 1;27(3):505-510. doi: 10.1016/j.bmcl.2016.12.032. Epub 2016 Dec 11. PMID: 28011223. 13: He Y, Wu M, Liu Y, Li Q, Li X, Hu L, Cen S, Zhou J. Identification of Triptophenolide from Tripterygium wilfordii as a Pan-antagonist of Androgen Receptor. ACS Med Chem Lett. 2016 Sep 28;7(12):1024-1027. doi: 10.1021/acsmedchemlett.6b00180. PMID: 27994731; PMCID: PMC5150686. 14: Wang T, Shen F, Su S, Bai Y, Guo S, Yan H, Ji T, Wang Y, Qian D, Duan JA. Comparative analysis of four terpenoids in root and cortex of Tripterygium wilfordii Radix by different drying methods. BMC Complement Altern Med. 2016 Nov 23;16(1):476. doi: 10.1186/s12906-016-1453-x. PMID: 27881165; PMCID: PMC5120441. 15: Xu WD, Li LQ, Li MM, Geng HC, Qin HB. Catalytic Asymmetric Formal Total Synthesis of (-)-Triptophenolide and (+)-Triptolide. Nat Prod Bioprospect. 2016 Jun;6(3):183-6. doi: 10.1007/s13659-016-0100-z. Epub 2016 Apr 20. PMID: 27095015; PMCID: PMC5385656. 16: Zhang XM, Chen YL, Yao YY, Li N, Liu YP, Liang XM. [Simultaneous determination of 5 compounds in Tripterygium hypoglaucum based on ultrasound- assisted ionic liquid coupled with HPLC]. Zhongguo Zhong Yao Za Zhi. 2016 Mar;41(5):879-886. Chinese. doi: 10.4268/cjcmm20160520. PMID: 28875643. 17: Tong Y, Su P, Zhao Y, Zhang M, Wang X, Liu Y, Zhang X, Gao W, Huang L. Molecular Cloning and Characterization of DXS and DXR Genes in the Terpenoid Biosynthetic Pathway of Tripterygium wilfordii. Int J Mol Sci. 2015 Oct 23;16(10):25516-35. doi: 10.3390/ijms161025516. PMID: 26512659; PMCID: PMC4632813. 18: Su P, Cheng Q, Wang X, Cheng X, Zhang M, Tong Y, Li F, Gao W, Huang L. Characterization of eight terpenoids from tissue cultures of the Chinese herbal plant, Tripterygium wilfordii, by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2014 Sep;28(9):1183-92. doi: 10.1002/bmc.3140. PMID: 25237706. 19: Liu Z, Zhao R, Zou Z. [Chemical constituents from root bark of Tripterygium hypoglaucum]. Zhongguo Zhong Yao Za Zhi. 2011 Sep;36(18):2503-6. Chinese. PMID: 22256754. 20: Goncalves S, Santoro S, Nicolas M, Wagner A, Maillos P, Himo F, Baati R. Cationic cyclization of 2-alkenyl-1,3-dithiolanes: diastereoselective synthesis of trans-decalins. J Org Chem. 2011 May 6;76(9):3274-85. doi: 10.1021/jo2001116. Epub 2011 Apr 13. PMID: 21446693.