Synonym
Chalinasterol; Ostreasterol; 24-Methylenecholesterol;
IUPAC/Chemical Name
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChi Key
INDVLXYUCBVVKW-PXBBAZSNSA-N
InChi Code
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18,20,22-26,29H,3,7-8,10-17H2,1-2,4-6H3/t20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
SMILES Code
CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)=C
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
398.68
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: Tsukagoshi Y, Suzuki H, Seki H, Muranaka T, Ohyama K, Fujimoto Y. Ajuga Δ24-Sterol Reductase Catalyzes the Direct Reductive Conversion of 24-Methylenecholesterol to Campesterol. J Biol Chem. 2016 Apr 8;291(15):8189-98. doi: 10.1074/jbc.M115.703470. Epub 2016 Feb 12. PubMed PMID: 26872973; PubMed Central PMCID: PMC4825020.
2: Nasu K, Takahashi K, Morisaki M, Fujimoto Y. Stereochemical fate of C-26 and C-27 during the conversion of isofucosterol to sitosterol and of 24-methylenecholesterol to campesterol and dihydrobrassicasterol in Oryza sativa cell cultures. Phytochemistry. 2000 Jun;54(4):381-5. PubMed PMID: 10897478.
3: Choe S, Dilkes BP, Gregory BD, Ross AS, Yuan H, Noguchi T, Fujioka S, Takatsuto S, Tanaka A, Yoshida S, Tax FE, Feldmann KA. The Arabidopsis dwarf1 mutant is defective in the conversion of 24-methylenecholesterol to campesterol in brassinosteroid biosynthesis. Plant Physiol. 1999 Mar;119(3):897-907. PubMed PMID: 10069828; PubMed Central PMCID: PMC32104.
4: Barbier M. Isolation of 24-methylenecholesterol-derived oxidation products from queen honeybee ovaries (Apis mellifica L.). J Chem Ecol. 1987 Jul;13(7):1681-7. doi: 10.1007/BF00980209. PubMed PMID: 24302336.
5: Teshima S, Kanazawa A, Yoshioka M, Kitahara K. Hypocholesterolemic effect of 24-methylenecholesterol and 7-cholestenol in the rat. J Steroid Biochem. 1974 Feb;5(1):69-72. PubMed PMID: 4845234.
6: Nes WR, Cannon JW, Thampi NS, Malya PA. Lack of mammalian reduction or alkylation of 24-methylenecholesterol. J Biol Chem. 1973 Jan 25;248(2):484-7. PubMed PMID: 4684690.
7: FAGERLUND UH, IDLER DR. Marine sterols. IX. Biosynthesis of 24-methylenecholesterol in clams. Can J Biochem Physiol. 1961 Sep;39:1347-55. PubMed PMID: 13697883.
8: BARBIER M, BOGDANOVSKY D. [Isolation and identification of 24-methylenecholesterol from the larva of queen bees and from royal jelly]. C R Seances Soc Biol Fil. 1961 May 29;252:3497-8. French. PubMed PMID: 13686806.
9: BERGMANN W, SCHEDL HP, LOW EM. Contributions to the study of marine products; chalinasterol. J Org Chem. 1945 Nov;10:587-93. PubMed PMID: 21009617.
