MedKoo Cat#: 598337 | Name: Tirucallol
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Description:

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

Tirucallol is an antiinflammatory isolated from Euphorbia lactea.

Chemical Structure

Tirucallol
CAS#514-46-5

Theoretical Analysis

MedKoo Cat#: 598337

Name: Tirucallol

CAS#: 514-46-5

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.72

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

Size Price Availability Quantity
1mg USD 330.00 2 Weeks
5mg USD 1,220.00 2 Weeks
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Related CAS #
No Data
Synonym
Tirucallol; NSC 403164; NSC403164; NSC-403164; (+)-Tirucallol
IUPAC/Chemical Name
(3S,5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-((S)-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-HGKXYCPESA-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+/m0/s1
SMILES Code
CC1(C)[C@@H](O)CC[C@]2(C)C3=C([C@]4(CC[C@H]([C@@]4(CC3)C)[C@@H](C)CC/C=C(C)\C)C)CC[C@@]12[H]
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

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
1: Onohuean H, Onohuean EF, Igbinoba S, Odoma S, Usman I, Ifie JE, Alagbonsi AI, Moyosore AA, Udom GJ, Agu PC, Aja PM, Ezeonwumelu JOC, Al-Kuraishy HM, Batiha GE, Osuntoki AA. In silico pharmacokinetic and therapeutic evaluation of Musa acuminata peels against aluminium chloride-induced hepatotoxicity in adult BALB/c mice. In Silico Pharmacol. 2024 May 23;12(1):46. doi: 10.1007/s40203-024-00216-1. PMID: 38800619; PMCID: PMC11116335. 2: Nicholson JM, Micalizio GC. Asymmetric Total Syntheses of Euphol and Tirucallol. Org Lett. 2023 Aug 4;25(30):5687-5691. doi: 10.1021/acs.orglett.3c02187. Epub 2023 Jul 21. PMID: 37477981; PMCID: PMC10654682. 3: Emmanuel O, Uche ME, Dike ED, Etumnu LR, Ugbogu OC, Ugbogu EA. A review on garcinia kola heckel: traditional uses, phytochemistry, pharmacological activities, and toxicology. Biomarkers. 2022 Mar;27(2):101-117. doi: 10.1080/1354750X.2021.2016974. Epub 2021 Dec 31. PMID: 34904497. 4: Qiao W, Feng W, Yang L, Li C, Qu X, Zhang Y. De Novo Biosynthesis of the Anticancer Compound Euphol in Saccharomyces cerevisiae. ACS Synth Biol. 2021 Sep 17;10(9):2351-2358. doi: 10.1021/acssynbio.1c00257. Epub 2021 Aug 27. PMID: 34445867. 5: Li G, Xu Q, Han K, Yan W, Huang C. Experimental evidence and network pharmacology-based analysis reveal the molecular mechanism of Tongxinluo capsule administered in coronary heart diseases. Biosci Rep. 2020 Oct 30;40(10):BSR20201349. doi: 10.1042/BSR20201349. PMID: 32990315; PMCID: PMC7560518. 6: de Souza LS, Puziol LC, Tosta CL, Bittencourt MLF, Ardisson JS, Kitagawa RR, Filgueiras PR, Kuster RM. Analytical methods to access the chemical composition of an Euphorbia tirucalli anticancer latex from traditional Brazilian medicine. J Ethnopharmacol. 2019 Jun 12;237:255-265. doi: 10.1016/j.jep.2019.03.041. Epub 2019 Mar 27. PMID: 30928500. 7: Fernandez-Arche A, Saenz MT, Arroyo M, de la Puerta R, Garcia MD. Topical anti-inflammatory effect of tirucallol, a triterpene isolated from Euphorbia lactea latex. Phytomedicine. 2010 Feb;17(2):146-8. doi: 10.1016/j.phymed.2009.05.009. Epub 2009 Jul 3. PMID: 19577446. 8: Loizou S, Paraschos S, Mitakou S, Chrousos GP, Lekakis I, Moutsatsou P. Chios mastic gum extract and isolated phytosterol tirucallol exhibit anti-inflammatory activity in human aortic endothelial cells. Exp Biol Med (Maywood). 2009 May;234(5):553-61. doi: 10.3181/0811-RM-338. Epub 2009 Feb 20. PMID: 19234052. 9: Xu ZH, Qin GW, Xu RS. An isopimarane diterpene from Euphorbia ebracteolata Hayata. J Asian Nat Prod Res. 2000;2(4):257-61. doi: 10.1080/10286020008041364. PMID: 11249607. 10: Siddiqui S, Siddiqui BS, Faizi S. Studies in the Chemical Constituents of Azadirachta indica Part II: Isolation and Structure of the New Triterpenoid Azadirachtol. Planta Med. 1985 Dec;51(6):478-80. doi: 10.1055/s-2007-969567. PMID: 17345262. 11: Nes WD, Wong RY, Benson M, Landrey JR, Nes WR. Rotational isomerism about the 17(20)-bond of steroids and euphoids as shown by the crystal structures of euphol and tirucallol. Proc Natl Acad Sci U S A. 1984 Sep;81(18):5896-900. doi: 10.1073/pnas.81.18.5896. PMID: 6592593; PMCID: PMC391822. 12: Kondo Y, Hatayama K, Ishiguro T, Takemoto T, Murakami S. [Studies on the constituents of Chinese drug "kanzui." 8. KMnO4 oxidation of euphol, tirucallol and beta-euphorbol]. Yakugaku Zasshi. 1967 Jan;87(1):21-5. Japanese. doi: 10.1248/yakushi1947.87.1_21. PMID: 6068623.