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5,7-Dihydroxycoumarin Sale

(Synonyms: 5,7-二羟基香豆素) 目录号 : GC61681

5,7-Dihydroxycoumarin是一种从Macarangatriloba的花序中分离出来的香豆素,具有抗菌活性。

5,7-Dihydroxycoumarin Chemical Structure

Cas No.:2732-18-5

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500 mg
¥450.00
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产品描述

5,7-Dihydroxycoumarin is a coumarin isolated from the inflorescences of Macaranga triloba. 5,7-Dihydroxycoumarin has antibacterial activities[1][2].

[1]. Ishak Zakaria, et al. Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba. Fitoterapia. 2012 Jul;83(5):968-72. [2]. Yi-Ping Chin, et al. Synthesis and evaluation of antibacterial activities of 5,7-dihydroxycoumarin derivatives. Arch Pharm (Weinheim). 2011 Jun;344(6):386-93.

Chemical Properties

Cas No. 2732-18-5 SDF
别名 5,7-二羟基香豆素
Canonical SMILES O=C1C=CC2=C(C=C(C=C2O)O)O1
分子式 C9H6O4 分子量 178.14
溶解度 储存条件 4°C, stored under nitrogen
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1 mM 5.6136 mL 28.0678 mL 56.1356 mL
5 mM 1.1227 mL 5.6136 mL 11.2271 mL
10 mM 0.5614 mL 2.8068 mL 5.6136 mL
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Research Update

Synthesis and evaluation of antibacterial activities of 5,7-Dihydroxycoumarin derivatives

Arch Pharm (Weinheim) 2011 Jun;344(6):386-93.PMID:21433055DOI:10.1002/ardp.201000233.

This study examines the synthesis and antibacterial activities of 5,7-Dihydroxycoumarin derivatives, whose structures were confirmed using analytical and spectral data. Twenty compounds were tested for their antibacterial activities against five microbial species such as E. coli, S. aureus, K. pneumonia, P. aeruginosa, and S. typhimurium were studied. Compounds 5 and 12 exhibited the most potent activity against Staphylococcus aureus with a MIC value of 2.5 µg/mL for each of the compounds.

Forming coumarin C-glycosides via biocatalysis: Characterization of a C-glycosyltransferase from Angelica decursiva

Biochem Biophys Res Commun 2022 Jul 23;614:85-91.PMID:35569380DOI:10.1016/j.bbrc.2022.05.008.

A glycosyl transferase, isolated from Angelica decursiva a medical herb rich in coumarin, shows C-glycosyl transferase activity by in vitro activity assay using 5,7-Dihydroxycoumarin as substrate, producing a C-glycosylated product at position C'8 along with the main product at C'6 position. Catalytic promiscuity assay shows that AdCGT also displays O- or C-glycosylation activity to other coumarins and flavonoids. When phloretin and 2,4,6-trihydroxyacetophenone were fed as substrates, AdCGT catalyzed the formation of di-C-glycosides. Therefore, AdCGT is a multifunctional glycosyltransferase with a broad substrate acceptability. This work highlights the potential of AdCGT as a catalyst for glycosylation of coumarin and reveals a new regio-selective C-glycosyltransferase, providing a basis for exploring the mechanism of coumarin glycosylation.

Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba

Fitoterapia 2012 Jul;83(5):968-72.PMID:22561914DOI:10.1016/j.fitote.2012.04.020.

A new flavanone derivative, malaysianone A (1), four prenylated flavanones, 6-prenyl-3'-methoxyeriodictyol (2), nymphaeol B (3), nymphaeol C (4) and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone (5), and two coumarins, 5,7-Dihydroxycoumarin (6) and scopoletin (7), were isolated from the dichloromethane extract of the inflorescences of Macaranga triloba. The structures of these compounds were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR and mass spectrometry. The cytotoxic activity of the compounds was tested against several cell lines, with 5 inhibiting very strongly the growth of HeLa and HL-60 cells (IC(50): 1.3 μg/ml and 3.3 μg/ml, respectively). Compound 5 also showed strong antiplasmodial activity (IC(50): 0.06 μM).

The sensitizing capacity of coumarins (III)

Contact Dermatitis 1989 Sep;21(3):141-7.PMID:2529098DOI:10.1111/j.1600-0536.1989.tb04726.x.

9 coumarins used as chemical reagents, laser dyes, in perfumery, cosmetics or occurring naturally, were investigated experimentally in guinea pigs to determine their contact sensitizing capacity. 5,7-Dihydroxycoumarin, limettin and 5,7-dihydroxy-4-methylcoumarin were found to be moderate sensitizers, while scoparone, isoscopoletin and 4-hydroxycoumarin were weak. The 3 laser dyes were completely negative. The results indicate that substitution in the 6 and 7 or 5 and 7 positions with 2 hydroxy groups supports allergenic capability, while other substituents (e.g., methoxy groups) in the same positions, or an additional (third) substituent, diminish activity.

[Study on non-flavonoids chemical constituents from Spatholobi Caulis]

Zhongguo Zhong Yao Za Zhi 2020 Mar;45(5):1120-1127.PMID:32237455DOI:10.19540/j.cnki.cjcmm.20200102.201.

To study the non-flavonoids chemical constituents in water extract of Spatholobi Caulis. Some purification and analysis techniques like silica gel, D101-macroporous adsorptive resins, and Sephadex LH-20 column chromatographies as well as reversed phase high-performance liquid chromatography were used to isolate and analyze the phenolic acid esters and other type compounds from Spatholobi Caulis integrally. The structures of these compounds were identified by spectroscopic techniques such as nuclear magnetic resonance and high resolution mass spectrometries. Twenty-seven compounds, including phenolic acid, coumarin, lignan, terpene, alkaloid, and steroid compounds, were isolated from ethyl acetate and n-butanol fractions in water extract of Spatholobi Caulis, and they were identified as β-sitosterol(1), feruli acid methyl ester(2), syringaresinol(3),(+)-medioresinol(4),(+)-epipinoresinol(5), p-acetylphenol(6), bolusanthin Ⅳ(7), evofolin B(8), salicylic acid(9), trans-p-hydroxy-cinnamic acid(10), abscisic acid(11), m-hydroxyphenol(12), C-veratroylglycol(13), p-hydroquinone(14), 8,9-dihydroxymegastigma-4,6-dien-3-one(15), p-hydroxybenzoic acid(16), 6,9-dihydroxymegastigma-4,7-dien-3-one(17), protocatechuic acid(18), protocatechuic acid methyl ester(19), 5,7-Dihydroxycoumarin(20), isolariciresinol(21), nicotinic acid(22), daucosterol(23),(+)-pinoresinol(24), stigmasterol(25), allantoin(26) and koaburaside(27), respectively. Furthermore, compounds 2-15, 19-22, 24 and 26 were isolated from genus Spatholobus for the first time.