Synonym
Lanosteryl caprylate;
IUPAC/Chemical Name
(3S,5R,10S,13R,14R,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-yl octanoate
InChi Key
JMQFHDCHYOCPQA-VRRDTQDMSA-N
InChi Code
InChI=1S/C38H64O2/c1-10-11-12-13-14-18-34(39)40-33-23-24-36(7)30-22-26-37(8)29(28(4)17-15-16-27(2)3)21-25-38(37,9)31(30)19-20-32(36)35(33,5)6/h16,28-29,32-33H,10-15,17-26H2,1-9H3/t28-,29-,32+,33+,36-,37-,38+/m1/s1
SMILES Code
CC1(C)[C@@H](OC(CCCCCCC)=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]
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
552.92
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.
| 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: Mosa RA, Cele ND, Mabhida SE, Shabalala SC, Penduka D, Opoku AR. In vivo antihyperglycemic activity of a lanosteryl triterpene from Protorhus longifolia. Molecules. 2015 Jul 22;20(7):13374-83. doi: 10.3390/molecules200713374. PubMed PMID: 26205060.
2: Mosa RA, Hlophe NB, Ngema NT, Penduka D, Lawal OA, Opoku AR. Cardioprotective potential of a lanosteryl triterpene from Protorhus longifolia. Pharm Biol. 2016 Dec;54(12):3244-3248. Epub 2016 Aug 30. PubMed PMID: 27572517.
3: Fox JE, Scott AI, Young DW. Photo-oxygenation of lanosteryl acetate. J Chem Soc Perkin 1. 1972;6:799-804. PubMed PMID: 5064150.
4: Mabhida SE, Mosa RA, Penduka D, Osunsanmi FO, Dludla PV, Djarova TG, Opoku AR. A Lanosteryl Triterpene from Protorhus longifolia Improves Glucose Tolerance and Pancreatic Beta Cell Ultrastructure in Type 2 Diabetic Rats. Molecules. 2017 Jul 26;22(8). pii: E1252. doi: 10.3390/molecules22081252. PubMed PMID: 28933769.
5: Wu TK, Wang TT, Chang CH, Liu YT, Shie WS. Importance of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase tyrosine 707 residue for chair-boat bicyclic ring formation and deprotonation reactions. Org Lett. 2008 Nov 6;10(21):4959-62. doi: 10.1021/ol802036c. Epub 2008 Oct 9. PubMed PMID: 18842050.
6: Weber N, Weitkamp P, Mukherjee KD. Steryl and stanyl esters of fatty acids by solvent-free esterification and transesterification in vacuo using lipases from Rhizomucor miehei, Candida antarctica, and Carica papaya. J Agric Food Chem. 2001 Nov;49(11):5210-6. PubMed PMID: 11714305.
