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3,3'-Di-O-methylellagic acid Sale

(Synonyms: 3,3'-O-二甲基鞣花酸,3,8-Di-O-methylellagic acid) 目录号 : GC35103

3,3'-Di-O-methylellagic acid 自来于 Euphorbia adenochlora,可选择性的抑制分枝杆菌耐酸性的形成而不阻碍其生长。3,3'-di-O-methylellagic acid 作为肝保护性化合物是由于它们的抗氧化作用。

3,3'-Di-O-methylellagic acid Chemical Structure

Cas No.:2239-88-5

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1mg
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产品描述

3,3'-Di-O-methylellagic acid obtained from Euphorbia adenochlora selectively inhibits the formation of acid-fastness in mycobacteria without retardation of their growth. 3,3'-di-O-methylellagic acid as a hepatoprotective compound is apparently due to its antioxidative effect[1][2].

[1]. Kondo Y, et al. Specific inhibition of formation of acid-fastness in mycobacteria by 3,3'-di-O-methylellagic acid. Experientia. 1979 May 15;35(5):599-600. [2]. Ito M, et al. Hepatoprotective compounds from Canarium album and Euphorbia nematocypha. Chem Pharm Bull (Tokyo). 1990 Aug;38(8):2201-3.

Chemical Properties

Cas No. 2239-88-5 SDF
别名 3,3'-O-二甲基鞣花酸,3,8-Di-O-methylellagic acid
Canonical SMILES O=C1C2=CC(O)=C(OC)C(O3)=C2C4=C(C3=O)C=C(O)C(OC)=C4O1
分子式 C16H10O8 分子量 330.25
溶解度 Soluble in DMSO 储存条件 4°C, protect from light
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1 mM 3.028 mL 15.14 mL 30.2801 mL
5 mM 0.6056 mL 3.028 mL 6.056 mL
10 mM 0.3028 mL 1.514 mL 3.028 mL
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Research Update

Disposition of the naturally occurring antimutagenic plant phenol, ellagic acid, and its synthetic derivatives, 3-O-decylellagic acid and 3,3'-Di-O-methylellagic acid in mice

Carcinogenesis 1986 Oct;7(10):1663-7.PMID:3093111DOI:10.1093/carcin/7.10.1663.

The effect of ellagic acid and some of its more lipophilic derivatives on the mutagenicity of (+/-)-7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9,10-tetrahydrobenz[a]pyrene was examined in Salmonella typhimurium TA100. Ellagic acid, 3,3'-Di-O-methylellagic acid, 4,4'-di-O-methylellagic acid and 3-O-decylellagic acid were found to have approximately equal antimutagenic activity. The tissue distribution and elimination of ellagic acid, 3,3'-Di-O-methylellagic acid and 3-O-decylellagic acid were examined in CD-1 mice. Little or no ellagic acid (less than 1 nmol/g) was found in blood, lung or liver after the oral administration by gavage of 300 mumol of ellagic acid per kg body weight of after feeding 1% of ellagic acid in the diet for 1 week. Following the i.p. administration of 120 mumol/kg of ellagic acid, the blood and lung levels of ellagic acid were 15-20 nmol/g at 30 min after the dose, and the concentrations of ellagic acid decreased to 1-3 nmol/g at 6-8 h after the dose. A portion of the administered i.p. dose precipitated in the abdominal cavity. After i.v. administration, ellagic acid was eliminated very rapidly from blood, lung and liver, and approximately 70% of the administered dose was recovered in the urine and feces as free ellagic acid and its conjugates. At 2 h after an i.v. injection of 60 mumol/kg of ellagic acid, 46% of the dose was recovered in the urine as ellagic acid and its conjugates. Of this amount, about half was excreted as free ellagic acid and half was excreted as conjugates. An additional 25% of the dose was recovered in the feces (mostly as free ellagic acid) after 7 h. The disposition of 3,3'-Di-O-methylellagic acid or 3-O-decylellagic acid after i.v. administration (32 mumol/kg) was examined and compared to the disposition of the same i.v. dose of ellagic acid. The concentrations of ellagic acid, 3,3'-Di-O-methylellagic acid and 3-O-decylellagic acid decreased rapidly in the blood, liver and lung, but the concentrations of 3-O-decylellagic acid in the lung throughout the experimental period (2-360 min) was on average 20- to 40-fold higher than the corresponding average concentrations of ellagic acid or 3,3'-Di-O-methylellagic acid.

Specific inhibition of formation of acid-fastness in mycobacteria by 3,3'-Di-O-methylellagic acid

Experientia 1979 May 15;35(5):599-600.PMID:87342DOI:10.1007/BF01960343.

3,3'-Di-O-methylellagic acid obtained from Euphorbia adenochlora selectively inhibited the formation of acid-fastness in mycobacteria without retardation of their growth. Gross reductions in contents of wax D, cord factor and free mycolic acids were found in the nonacid-fast bacilli compared with the normal ones.

Alpha-glucosidase inhibitors ellagic acid derivatives with immunoinhibitory properties from Terminalia superba

Chem Pharm Bull (Tokyo) 2008 Jun;56(6):847-50.PMID:18520093DOI:10.1248/cpb.56.847.

Fractionation of stem barks of Terminalia superba yielded two new ellagic acid derivatives, 3,4'-di-O-methylellagic acid 3'-O-beta-D-xylopyranoside (1) and 4'-O-galloy-3,3'-di-O-methylellagic acid 4-O-beta-D-xylopyranoside (2) together with known 3,3'-Di-O-methylellagic acid, ellagic acid and 3,3'-Di-O-methylellagic acid 4'-O-beta-D-xylopyranoside. Compounds (1) and (2) showed significant alpha-glucosidase inhibition activity and possessed significant immunoinhibitory activities with no cytotoxic effects.

Identification of ellagic acid derivatives in methanolic extracts from Qualea species

Z Naturforsch C J Biosci 2008 Nov-Dec;63(11-12):794-800.PMID:19227825DOI:10.1515/znc-2008-11-1203.

The methanolic extract from the barks of the medicinal plant Qualea parviflora (Vochysiaceae) was fractionated by column chromatography over silica gel followed by gel permeation over Sephadex LH-20 to give 3,3'-di-O-methylellagic acid-4-O-beta-D-glucopyranoside (1), 3-O-methylellagic acid-4'-O-alpha-L-rhamnopyranoside (2), 3,3',4-tri-O-methylellagic acid-4'-O-beta-D-glucopyranoside (3), and 3,3'-Di-O-methylellagic acid (4), together with triterpenes and saponins. We also performed comparative analyses among this species and Q. grandiflora and Q. multiflora using high-pressure liquid chromatography. The biological assays showed that, when compared to the standard ellagic acid, compounds 1-4 are less cytotoxic but have a lower capacity of stimulating murine peritoneal macrophages to release nitric oxide and tumoural-alpha necrose factor.

Chemical constituents with antibacterial activity from Euphorbia sororia

Nat Prod Res 2008 Mar 10;22(4):353-9.PMID:18322851DOI:10.1080/14786410701838114.

A group of ceramide (1) was isolated from the aerial parts of Euphorbia sororia. On the basis of spectroscopic data, chemical methods and GC-MS analysis, the structure of 1 was characterised as (2S,3S,4R,8E)-2-(eicosanoyl approximately octacosanoyl amino)-1,3,4-octadecanetriol-8-ene. In addition, four known ellagic acid derivatives 3,3'-Di-O-methylellagic acid (2), 3,3',4'-tri-O-methylellagic acid (3), 4-O-sulfooxy-3,3'-di-O-methylellagic acid (4) and 4-O-sulfooxy- 3,3',4'-tri-O-methylellagic acid (5) were isolated from the plant. Biological screening of all compounds revealed moderate antibacterial activity.