1690-62-6

Usage

Uses

Used in Menopausal Symptom Treatment:
3-Hydroxy-9-methoxycoumestan is used as a phytoestrogen for alleviating menopausal symptoms due to its estrogenic activity, which can help balance hormone levels and reduce symptoms such as hot flashes and night sweats.
Used in Osteoporosis Treatment:
In the healthcare industry, 3-Hydroxy-9-methoxycoumestan is used as a potential treatment for osteoporosis, leveraging its estrogenic properties to support bone health and prevent bone loss.
Used in Breast Cancer Therapy:
3-Hydroxy-9-methoxycoumestan is used as a potential therapeutic agent in breast cancer treatment, with its antiestrogenic activity potentially inhibiting the growth of estrogen receptor-positive tumors.
Used in Antioxidant and Anti-inflammatory Applications:
3-Hydroxy-9-methoxycoumestan is used as an antioxidant and anti-inflammatory agent, with its properties potentially beneficial in reducing oxidative stress and inflammation in various conditions.
Used in Cholesterol Regulation:
In the pharmaceutical industry, 3-Hydroxy-9-methoxycoumestan is used as a cholesterol-regulating agent, with its potential to modulate cholesterol levels and support cardiovascular health.
Further research is necessary to fully understand the properties and potential applications of 3-Hydroxy-9-methoxycoumestan, ensuring its safe and effective use in various therapeutic areas.

InChI:InChI=1/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

Upstream product

• 112116-05-9 3-benzyloxy-9-methoxy-benzofuro[3,2-c]chromen-6-one 
• 54300-95-7 7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-2H-chromen-2-one 
• 32383-76-9 (-)-3-hydroxy-9-methoxypterocarpan 
• 102661-84-7 3-benzyloxy-9-hydroxy-benzofuro[3,2-c]chromen-6-one 
• 35826-57-4 Coumestrol diacetate 
• 102543-23-7 9-acetoxy-3-benzyloxy-benzofuro[3,2-c]chromen-6-one 
• 1276694-74-6 C₁₈H₂₀O₄ 
• 1276694-76-8 C₁₉H₁₆O₅ 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 20503-09-7 2-(2-hydroxy-4-methoxyphenyl)acetic acid 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 42345-56-2 4,7-dihydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one 
• 104-01-8 4-Methoxyphenylacetic acid 
• 108-46-3 recorcinol 

Relevant academic research and scientific papers

3, 9-di-O-substituted coumestrols incorporating basic amine side chains act as novel apoptosis inducers with improved pharmacological selectivity

There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to experimental evidence that it has been shown to stimulate MCF-7 cell proliferation via agonist effect on estrogen receptor at low concentration. Herein, to disconnect the ER interaction and apoptosis-specific mechanism of coumestrol, various 3, 9-di-O-substituted coumestrols (7a-7e) and their furan ring-opened analogs (5a-5e) were synthesized and assessed for antiproliferative properties. Attachment of a dimethylamine-containing side chain to 3-O of coumestrol led to the most promising compound 7e with improved antiproliferative activity (1.7-fold increase) against MCF-7 cells, decreased estrogen activity (>20 times weaker ERα binder) and a novel action to induce apoptosis. Mechanistic studies revealed that 7e is a tubulin polymerization inhibitor, which could arrest cell cycle at G2/M phase and induce apoptosis along with the decrease of mitochondrial membrane potential. In summary, such subtle modifications to the 3, 9-di-hydroxyl groups of coumestrol allow the generation of a novel apoptosis inducer with distinct pharmacological properties, providing an excellent starting point to future development of novel tumor-vascular disrupting agents targeting tubulin.

BIOSYNTHESIS OF PTEROCARPAN, ISOFLAVAN AND COUMESTAN METABOLITES OF MEDICAGO SATIVA: THE ROLE OF AN ISOFLAV-3-ENE

Feeding experiments in CuCl2- and UV-treated lucerne (Medicago sativa) seedlings have shown that demethylhomopterocarpin- is incorporated into vestitol and sativan without any loss of 3H label, and vestitol- is similarly incorporated into demethylhomopterocarpin and sativan with retention of the 3H:14C ratio.Thus, an isoflav-3-ene intermediate in the interconversion of demethylhomopterocarpin and vestitol is excluded. 7,2'-Dihydroxy-4'-methoxyisoflav-3-ene- was not incorporated into the three phytoalexins, but was an excellent precursor of 9-O-methylcoumestrol, as also was 7,2'-dihydroxy-4'-methoxyisoflav-3-en-2-one-.A biosynthetic pathway to coumestans via isoflav-3-enes and 3-arylcoumarins is proposed.A metabolic scheme in M. sativa interrelating eight classes of naturally occurring isoflavonoids is presented. - Key Word Index: Medicago sativa; Leguminosae; lucerne; biosynthesis; phytoalexin; pterocarpan; isoflavan; coumestan; demethylhomopterocarpin; vestitol; sativan; 9-O-methylcoumestrol.

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Coumadin female phenol split-ring analogue and its medical use

The invention relates to the field of pharmaceutical chemistry, in particular to a coumestrol open-ring analogue with structures as shown in general formulae I and II and a medical application thereof, especially an application to the preparation of drugs as angiogenesis inhibition and vascular disruption agents.

Copper-mediated synthesis of coumestans via C(sp2)-H functionalization: Protective group free route to coumestrol and 4′-O-methylcoumestrol

A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for C[sbnd]H functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol.

Synthesis of coumestan derivatives via FeCl3-mediated oxidative ring closure of 4-hydroxy coumarins

A concise and efficient approach to the syntheses of coumestan analogues has been developed. The underpinning strategy involves a FeCl 3-mediated direct intramolecular oxidative annellation of 4-hydroxy-3-phenyl-2H-chromen-2-one derivatives. Utilizing this synthetic protocol, a variety of coumestan derivatives were conveniently obtained from readily available reagents.

Diarylheptanoid and Other Phenolic Constituents of Centrolobium Species

The heartwood of a specimen of Centrolobium tomentosum Benth (Leguminosae) has given (-)-centrolobine (1a), (-)-de-O-methylcentrolobine (1b), (-)-centrolobol (2), piceatannol (3) and the isoflavone formononetin (4).The heartwood of a second Centrolobium species, which could not be identified further at the U.S.Forest Products Laboratory, yielded (+)-centrolobine, (+)-de-O-methylcentrolobine, (+)-centrolobol, formononetin, 4',7-dihydroxyflavanone (5), 3-hydroxy-9-methoxypterocarpan (6), and minor amounts of a new dihydric phenol.This was identified by n.m.r. and X-ray diffraction measurements as 2-(2'-hydroxy-4'-methoxyphenyl)benzofuran-6-ol (8).