Ethyl Orsellinate
(Synonyms: 山梨酸乙酯) 目录号 : GC40699
A lichen metabolite
Cas No.:2524-37-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ethyl orsellinate is a lichen metabolite and a derivative of lecanoric acid that has antiproliferative activities. It inhibits the proliferation of human Hep-2 larynx carcinoma, MCF-7 breast cancer, and 786-0 kidney carcinoma cells, as well as B16-F10 murine melanoma and non-cancerous Vero cells (IC50s = 31.2, 70.3, 47.5, 64.8, and 28.1 µg/ml, respectively). Ethyl orsellinate is toxic to brine shrimp (A. salina) with an LC50 value of 495 µM.
| Cas No. | 2524-37-0 | SDF | |
| 别名 | 山梨酸乙酯 | ||
| Canonical SMILES | CC1=C(C(OCC)=O)C(O)=CC(O)=C1 | ||
| 分子式 | C10H12O4 | 分子量 | 196.2 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml,PBS (pH 7.2): 0.1 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.0968 mL | 25.4842 mL | 50.9684 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
[Determination of atranol, lecanorin, Ethyl Orsellinate and methyl orsellinate in Usnea diffracta by RP-HPLC]
Zhongguo Zhong Yao Za Zhi 2011 Aug;36(16):2233-5.PMID:22097337doi
Objective: To develop a RP-HPLC method for determining the contents of atranol, lecanorin, Ethyl Orsellinate and methyl orsellinate in Usnea diffracta. Method: A Kromasil-C18 column (4.6 mm x 250 mm, 5 microm) was used at 25 degrees C with the mobile phases of acetonitrile -1% acetic acid in a gradient manner. The flow rate was set at 1.0 mL x min(-1). The detection wavelength was 280 nm. Result: The correlation coefficients of atranol, lecanorin, Ethyl Orsellinate, and methyl orsellinate were higher than 0.999. Recoveries were from 102.9% to 95.30%; with RSD from 2.3% to 1.9%. Conclusion: The method is quick, simple and repeatable for simultaneous determination of atranol, lecanorin, Ethyl Orsellinate and methyl orsellinate in U. diffracta.
Cytotoxic activity of orsellinates
Z Naturforsch C J Biosci 2006 Sep-Oct;61(9-10):653-7.PMID:17137109DOI:10.1515/znc-2006-9-1007.
The series of 2,4-dihydroxy-6-methylbenzoates 2-10 (methyl to hexyl orsellinates) prepared by alcoholysis of lecanoric acid (1)--a natural product from the lichen Parmotrema tinctorum (Nyl.) Hale - was submitted to the brine shrimp lethality test (BST), which was also performed for 2,4-dihydroxy-6-methylbenzoic acid (11) (orsellinic acid) and the derivative ethyl-2-hydroxy-4-methoxy-6-methylbenzoate (12) (4-methoxy-ethyl orsellinate), in order to detect new substances with probable antineoplasic activity. Results showed that chain elongation--increase in lipophilicity (log P)--causes a rise in the cytotoxic activity of orsellinates. Hexyl orsellinate (7) showed the highest cytotoxic activity (LC50 = 31 microM). A correlation between lipophilicity (log P) and cytotoxic activity (log 1/LC50) is presented. Compounds with ramified chains--iso-propyl, sec-butyl and tert-butyl orsellinates (8-10)--were less active than those with the correspondent linear chain. The activities presented by 4-methoxy-ethyl orsellinate (12) and Ethyl Orsellinate (3) suggest that the hydroxy group at the C-4 position causes effect in the cytotoxic activity of orsellinates against Artemia salina.
In vitro antitumour activity of orsellinates
Z Naturforsch C J Biosci 2010 Jan-Feb;65(1-2):43-8.PMID:20355320DOI:10.1515/znc-2010-1-208.
Lichen phenolic compounds exhibit antioxidant, antimicrobial, antiproliferative, and cytotoxic activities. The purpose of this study was to evaluate the anticancer activity of lecanoric acid, a secondary metabolite of the lichen Parmotrema tinctorum, and its derivatives, orsellinates, obtained by structural modification. A cytotoxicity assay was carried out in vitro with sulforhodamine B (SRB) using HEp-2 larynx carcinoma, MCF7 breast carcinoma, 786-0 kidney carcinoma, and B16-F10 murine melanoma cell lines, in addition to a normal (Vero) cell line in order to calculate the selectivity index of the compounds. n-Butyl orsellinate was the most active compound, with IC50 values (the concentration that inhibits 50% of growth) ranging from 7.2 to 14.0 microg/mL, against all the cell lines tested. The compound was more active (IC50 = 11.4 microg/mL) against B16-F10 cells than was cisplatin (12.5 microg/mL). Conversely, lecanoric acid and methyl orsellinate were less active against all cell lines, having an IC50 value higher than 50 microg/mL. Ethyl Orsellinate was more active against HEp-2 than against MCF7, 786-0, or B16-F10 cells. The same pattern was observed for n-propyl and n-butyl orsellinates. n-Pentyl orsellinate was less active than n-propyl or n-butyl orsellinates against HEp-2 cells. The orsellinate activity increased with chain elongation (from methyl to n-butyl), a likely consequence of an increase in lipophilicity. The results revealed that the structural modification of lecanoric acid increases the cytotoxic activity of the derivatives tested.
A new epicatechin glucopyranoside derivative from Styrax suberifolius
Nat Prod Res 2020 Jul;34(14):1977-1983.PMID:30732479DOI:10.1080/14786419.2019.1569011.
A new derivative of epicatechin glucopyranoside, (2R,3R)-3,7,4'-trihydroxy-5,3'-dimethoxyflavan 7-O-β-d-glucopyranoside (1), together with three mononuclear phenolic acid esters, methyl orsellinate (2), Ethyl Orsellinate (3) and methyl β-orcinolcarboxylate (4) were isolated from the bark of Styrax suberifolius. The structures of 1-4 were determined on the basis of extensive analysis of NMR and MS spectra combined with chemical hydrolysis. The antifungal activities of the isolated compounds against three plant pathogenic fungi, Alternaria solani, Fusarium oxysporum and Phomopsis cytospore were evaluated using radial growth inhibition assay. Compounds 2, 3 and 4 exerted selective inhibitory activities against the tested fungi. Among of them, methyl β-orcinolcarboxylate (4) exhibited obvious inhibitory effect against P. cytospore, with an inhibition rate of 86.72% at 100 μg/ml.
Are atranols the only skin sensitizers in oakmoss? A systematic investigation using non-animal methods
Toxicol In Vitro 2021 Feb;70:105053.PMID:33212168DOI:10.1016/j.tiv.2020.105053.
Oakmoss and treemoss absolutes are the major natural extracts of concern as potential sources of skin sensitizers in cosmetics and personal care products (PCP). Two single constituents, atranol and chloroatranol, have been identified as primary culprits in both lichens, and industrial self-regulation has been proposed to limit their contents to less than 100 ppm. Nonetheless, evidence points to the presence of additional candidate skin sensitizers in these multicomponent extracts. These observations, along with a lack of data from non-animal alternative methods and the chemical variability of commercial absolutes, prompted further investigation of oakmoss absolute along with altranol-like compounds in these extracts. The major chemical constituents of a commercial sample were identified by two independent analytical techniques, GC-MS and HPLC-DAD-MS. The crude oakmoss extract and pure compounds were assayed with two in chemico methods (HTS-DCYA and DPRA) to gauge their chemical reactivity. Activation of inflammatory responses in vitro was also investigated by KeratinoSens™ and human cell line activation tests (h-CLAT). Based on weight of evidence, orcinol, Ethyl Orsellinate, and usnic acid were classified as candidate sensitizers, along with both atranols and oakmoss extract.