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MedKoo Cat#: 146215 | Name: Coumestan

Description:

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

Coumestan is a plant-derived polyphenolic compound and the core structure of a class of phytoestrogens known as coumestans, which includes biologically active compounds like coumestrol. Found in legumes such as alfalfa and clover, coumestan exhibits estrogen-like activity by binding to estrogen receptors, particularly ERβ, influencing hormonal signaling pathways. Its mechanism involves modulation of gene expression related to estrogenic activity, antioxidant defense, and potential antiproliferative effects in hormone-sensitive tissues. Applications of coumestan are mainly in nutritional science and medical research, where it is studied for its potential benefits in hormone regulation, cancer prevention, and menopausal symptom relief.

Chemical Structure

Coumestan
Coumestan
CAS#479-12-9

Theoretical Analysis

MedKoo Cat#: 146215

Name: Coumestan

CAS#: 479-12-9

Chemical Formula: C15H8O3

Exact Mass: 236.0473

Molecular Weight: 236.23

Elemental Analysis: C, 76.27; H, 3.41; O, 20.32

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
Coumestan;
IUPAC/Chemical Name
6H-benzofuro[3,2-c]chromen-6-one
InChi Key
JBIZUYWOIKFETJ-UHFFFAOYSA-N
InChi Code
1S/C15H8O3/c16-15-13-9-5-1-3-7-11(9)17-14(13)10-6-2-4-8-12(10)18-15/h1-8H
SMILES Code
O=C1OC2=C(C=CC=C2)C3=C1C4=C(O3)C=CC=C4
Appearance
To be determined
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 236.23 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: Canivenc-Lavier MC, Bennetau-Pelissero C. Phytoestrogens and Health Effects. Nutrients. 2023 Jan 9;15(2):317. doi: 10.3390/nu15020317. PMID: 36678189; PMCID: PMC9864699. 2: Lun S, Xiao S, Zhang W, Wang S, Gunosewoyo H, Yu LF, Bishai WR. Therapeutic potential of coumestan Pks13 inhibitors for tuberculosis. Antimicrob Agents Chemother. 2023 May 1;95(5):e02190-20. doi: 10.1128/AAC.02190-20. Epub 2021 Feb 8. PMID: 33558290; PMCID: PMC8092898. 3: Patra S, Gorai S, Pal S, Ghosh K, Pradhan S, Chakrabarti S. A review on phytoestrogens: Current status and future direction. Phytother Res. 2023 Jul;37(7):3097-3120. doi: 10.1002/ptr.7861. Epub 2023 May 29. PMID: 37246823. 4: Achari A, Chatterjee S, Dey S, Kundu TK, Jaisankar P. Catecholase-catalyzed synthesis of wedelolactone, a natural coumestan and its analogs. Org Biomol Chem. 2022 Dec 21;21(1):89-92. doi: 10.1039/d2ob02081e. PMID: 36477994. 5: Zhang W, Lun S, Liu LL, Xiao S, Duan G, Gunosewoyo H, Yang F, Tang J, Bishai WR, Yu LF. Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis. Part II. J Med Chem. 2019 Apr 11;62(7):3575-3589. doi: 10.1021/acs.jmedchem.9b00010. Epub 2019 Mar 27. PMID: 30875203. 6: Xi GL, Liu ZQ. Coumestan inhibits radical-induced oxidation of DNA: is hydroxyl a necessary functional group? J Agric Food Chem. 2014 Jun 18;62(24):5636-42. doi: 10.1021/jf500013v. Epub 2014 Jun 9. PMID: 24911109. 7: Tu Y, Tan L, Lu T, Wang K, Wang H, Han B, Zhao Y, Chen H, Li Y, Chen H, Chen M, He C. Glytabastan B, a coumestan isolated from Glycine tabacina, alleviated synovial inflammation, osteoclastogenesis and collagen-induced arthritis through inhibiting MAPK and PI3K/AKT pathways. Biochem Pharmacol. 2022 Mar;197:114912. doi: 10.1016/j.bcp.2022.114912. Epub 2022 Jan 12. PMID: 35032460. 8: Chai MY. A new bioactive coumestan from the seeds of Psoralea corylifolia. J Asian Nat Prod Res. 2020 Mar;22(3):295-301. doi: 10.1080/10286020.2018.1563073. Epub 2019 Jan 24. PMID: 30678490. 9: Zhang W, Lun S, Wang SS, Cai YP, Yang F, Tang J, Bishai WR, Yu LF. Structure- Based Optimization of Coumestan Derivatives as Polyketide Synthase 13-Thioesterase(Pks13-TE) Inhibitors with Improved hERG Profiles for Mycobacterium tuberculosis Treatment. J Med Chem. 2022 Oct 13;65(19):13240-13252. doi: 10.1021/acs.jmedchem.2c01064. Epub 2022 Sep 29. PMID: 36174223. 10: Kurzer MS, Xu X. Dietary phytoestrogens. Annu Rev Nutr. 1997;17:353-81. doi: 10.1146/annurev.nutr.17.1.353. PMID: 9240932. 11: Tu Y, Wang K, Tan L, Han B, Hu Y, Ding H, He C. Dolichosin A, a coumestan isolated from Glycine tabacina, inhibits IL-1β-induced inflammation in SW982 human synovial cells and suppresses RANKL-induced osteoclastogenesis: From network pharmacology to experimental pharmacology. J Ethnopharmacol. 2020 Aug 10;258:112855. doi: 10.1016/j.jep.2020.112855. Epub 2020 May 4. PMID: 32376366. 12: Li Y, Chen H, Liu J, Luo XL, Xiao CJ, Jiang B. A new prenylated coumestan from the roots of Campylotropis hirtella. J Asian Nat Prod Res. 2021 Aug;23(8):789-795. doi: 10.1080/10286020.2020.1779706. Epub 2020 Jul 2. PMID: 32614662. 13: Djafarou S, Boulebd H. The radical scavenger capacity and mechanism of prenylated coumestan-type compounds: a DFT analysis. Free Radic Res. 2022 Mar- Apr;56(3-4):273-281. doi: 10.1080/10715762.2022.2085097. Epub 2022 Jun 13. PMID: 35696761. 14: Duncan AM, Phipps WR, Kurzer MS. Phyto-oestrogens. Best Pract Res Clin Endocrinol Metab. 2003 Jun;17(2):253-71. doi: 10.1016/s1521-690x(02)00103-3. PMID: 12787551. 15: Livingston AL. Forage plant estrogens. J Toxicol Environ Health. 1978 Mar- May;4(2-3):301-24. doi: 10.1080/15287397809529663. PMID: 351201. 16: Giang LT, Park S, Cuc NT, Tai BH, Kiem PV, Hang NTM, Ban NK, Cuong PV, Nhiem NX. Bithiophene and coumestan derivatives from Eclipta prostrata (L.) L. and their hepatoprotective activity. J Asian Nat Prod Res. 2024 Nov;26(11):1381-1387. doi: 10.1080/10286020.2024.2364912. Epub 2024 Jun 13. PMID: 38869195. 17: Ha NM, Hop NQ, Son NT. Wedelolactone: A molecule of interests. Fitoterapia. 2023 Jan;164:105355. doi: 10.1016/j.fitote.2022.105355. Epub 2022 Nov 21. PMID: 36410612. 18: Shinde VN, Rangan K, Kumar D, Kumar A. Palladium-Catalyzed Weakly Coordinating Lactone-Directed C-H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives. J Org Chem. 2021 Jul 16;86(14):9755-9770. doi: 10.1021/acs.joc.1c01097. Epub 2021 Jun 28. PMID: 34181412. 19: Wang MQ, Zhang KH, Liu FL, Zhou R, Zeng Y, Chen AL, Yu Y, Xia Q, Zhu CC, Lin CZ. Wedelolactone alleviates cholestatic liver injury by regulating FXR-bile acid-NF-κB/NRF2 axis to reduce bile acid accumulation and its subsequent inflammation and oxidative stress. Phytomedicine. 2024 Jan;122:155124. doi: 10.1016/j.phymed.2023.155124. Epub 2023 Sep 29. PMID: 38014837. 20: Qwebani-Ogunleye T, Kolesnikova NI, Steenkamp P, de Koning CB, Brady D, Wellington KW. A one-pot laccase-catalysed synthesis of coumestan derivatives and their anticancer activity. Bioorg Med Chem. 2017 Feb 1;25(3):1172-1182. doi: 10.1016/j.bmc.2016.12.025. Epub 2016 Dec 21. PMID: 28041801.

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