Euphol

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

MedKoo CAT#: 598338

CAS#: 514-47-6

Description: Euphol is an alcohol tetracyclic triterpene which is considered to have anti-inflammatory action. Oral administration of euphadienol consistently reduces and limits the severity and development of experimental autoimmune encephalomyelitis (EAE) which is an established model of Multiple sclerosis (MS). Euphadienol has been found to inhibit various autonomic pressor and depressor responses in dogs and rats.

Chemical Structure

img
Euphol
CAS# 514-47-6
Instruction

Theoretical Analysis

MedKoo Cat#: 598338
Name: Euphol
CAS#: 514-47-6
Chemical Formula: C30H50O
Exact Mass: 426.39
Molecular Weight: 426.720
Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Euphol; NSC 36571; NSC-36571; NSC36571;

IUPAC/Chemical Name: (3S,5R,10R,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methylhept-5-en-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

InChi Key: CAHGCLMLTWQZNJ-CXSQPFRJSA-N

InChi Code: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28+,29-,30-/m1/s1

SMILES Code: C/C(C)=C\CC[C@@H](C)[C@@H](CC1)[C@]2(C)[C@@]1(C)C3=C([C@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC3)CC2

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 426.72 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Dutra RC, Bicca MA, Segat GC, Silva KA, Motta EM, Pianowski LF, Costa R, Calixto JB. The antinociceptive effects of the tetracyclic triterpene euphol in inflammatory and neuropathic pain models: The potential role of PKCε. Neuroscience. 2015 Sep 10;303:126-37. doi: 10.1016/j.neuroscience.2015.06.051. Epub 2015 Jul 2. PubMed PMID: 26143011.

2: Chen CL, Chen YP, Lin MW, Huang YB, Chang FR, Duh TH, Wu DC, Wu WC, Kao YC, Yang PH. Euphol from Euphorbia tirucalli Negatively Modulates TGF-β Responsiveness via TGF-β Receptor Segregation inside Membrane Rafts. PLoS One. 2015 Oct 8;10(10):e0140249. doi: 10.1371/journal.pone.0140249. eCollection 2015. PubMed PMID: 26448474; PubMed Central PMCID: PMC4598150.

3: Xie X, Li Y, Gao D, Zhang Y, Ren Y. Quantitative determination of euphol in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomed Chromatogr. 2014 Sep;28(9):1229-34. doi: 10.1002/bmc.3151. PubMed PMID: 25237707.

4: Wang L, Wang G, Yang D, Guo X, Xu Y, Feng B, Kang J. Euphol arrests breast cancer cells at the G1 phase through the modulation of cyclin D1, p21 and p27 expression. Mol Med Rep. 2013 Oct;8(4):1279-85. doi: 10.3892/mmr.2013.1650. Epub 2013 Aug 22. PubMed PMID: 23969579.

5: Abdel-Sattar E, Abou-Hussein D, Petereit F. Chemical Constituents from the Leaves of Euphorbia ammak Growing in Saudi Arabia. Pharmacognosy Res. 2015 Jan-Mar;7(1):14-7. doi: 10.4103/0974-8490.147136. PubMed PMID: 25598629; PubMed Central PMCID: PMC4285643.

6: Singh GB, Singh S, Sharma ML, Suri OP, Chopra CL, Ammon HP. Hypotensive activity of 8,24-euphadien-3 beta-ol (euphol). Planta Med. 1989 Dec;55(6):498-500. PubMed PMID: 2616667.

7: Yasukawa K, Akihisa T, Yoshida ZY, Takido M. Inhibitory effect of euphol, a triterpene alcohol from the roots of Euphorbia kansui, on tumour promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. J Pharm Pharmacol. 2000 Jan;52(1):119-24. PubMed PMID: 10716613.

8: Luz LEC, Kanunfre CC, Paludo KS, da Silva Justo A, Petry VK, Lemes BM, Barison A, Nepel A, Wang M, Avula B, Khan IA, Beltrame FL. Cytotoxic biomonitored study of Euphorbia umbellata (Pax) Bruyns. J Ethnopharmacol. 2016 May 13;183:29-37. doi: 10.1016/j.jep.2016.02.025. Epub 2016 Feb 22. PubMed PMID: 26906968.

9: Munhoz AC, Minozzo BR, Cruz LS, Oliveira TL, Machado WM, Pereira AV, Fernandes D, Manente FA, Vellosa JC, Nepel A, Barison A, Beltrame FL. Chemical and pharmacological investigation of the stem bark of Synadenium grantii. Planta Med. 2014 Apr;80(6):458-64. doi: 10.1055/s-0034-1368300. Epub 2014 Mar 31. PubMed PMID: 24687740.

10: de Oliveira TL, Munhoz AC, Lemes BM, Minozzo BR, Nepel A, Barison A, Fávero GM, Campagnoli EB, Beltrame FL. Antitumoural effect of Synadenium grantii Hook f. (Euphorbiaceae) latex. J Ethnopharmacol. 2013 Oct 28;150(1):263-9. doi: 10.1016/j.jep.2013.08.033. Epub 2013 Sep 2. PubMed PMID: 24008110.

11: Zhao M, Wu S, Li J, Tang WX, Wang JL, Zhang SJ. [Chemical constituents from Euphorbia lunulata]. Zhongguo Zhong Yao Za Zhi. 2014 Jun;39(12):2289-94. Chinese. PubMed PMID: 25244761.

12: King AR, Dotsey EY, Lodola A, Jung KM, Ghomian A, Qiu Y, Fu J, Mor M, Piomelli D. Discovery of potent and reversible monoacylglycerol lipase inhibitors. Chem Biol. 2009 Oct 30;16(10):1045-52. doi: 10.1016/j.chembiol.2009.09.012. PubMed PMID: 19875078; PubMed Central PMCID: PMC3034734.

13: Ruan HL, Zhang Y, Zhang YH, Pi HF, Wu JZ. [Studies on constituents from roots of Euphorbia hylonoma]. Zhongguo Zhong Yao Za Zhi. 2006 May;31(9):742-4. Chinese. PubMed PMID: 17048682.

14: Silva VAO, Rosa MN, Miranda-Gonçalves V, Costa AM, Tansini A, Evangelista AF, Martinho O, Carloni AC, Jones C, Lima JP, Pianowski LF, Reis RM. Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells. Invest New Drugs. 2018 Jun 22. doi: 10.1007/s10637-018-0620-y. [Epub ahead of print] PubMed PMID: 29931585.

15: Gewali MB, Pilapitiya U, Hattori M, Namba T. Analysis of a thread used in the Kshara Sutra treatment in the Ayurvedic medicinal system. J Ethnopharmacol. 1990 May;29(2):199-206. PubMed PMID: 2374431.

16: Shi DY, Han LJ, Sun J, Yang YC, Shi JG, Fan X. [Studies on chemical constitutes of green alga Chaetomorpha basiretorsa and their bioactivity]. Zhongguo Zhong Yao Za Zhi. 2005 Aug;30(15):1162-5. Chinese. PubMed PMID: 16201690.

17: Cao D, Su YL, Yang JS. [Triterpene constituents from Euphorbia nematocypha Hand-Mazz]. Yao Xue Xue Bao. 1992;27(6):445-51. Chinese. PubMed PMID: 1442072.

18: Guo ZJ, Zuo JF, Bo XQ, Sun QS. [Study on chemical constituents of Euphorbia hylonoma hand. -Mazz]. Zhong Yao Cai. 2007 Apr;30(4):412-5. Chinese. PubMed PMID: 17674791.

19: Haba H, Marcourt L, Benkhaled M, Long C. Minor ent-abietane diterpenoids from Euphorbia guyoniana. Nat Prod Commun. 2013 Nov;8(11):1519-22. PubMed PMID: 24427931.

20: Mallavadhani UV, Satyanarayana KV, Mahapatra A, Sudhakar AV. A new tetracyclic triterpene from the latex of Euphorbia nerifolia. Nat Prod Res. 2004 Feb;18(1):33-7. PubMed PMID: 14974615.