IUPAC/Chemical Name
(1aS,4Z,10aS,11E,14aS)-1a,5,8,12-tetramethyl-1a,2,3,6,7,9,10a,13,14,14a-decahydrooxireno[2',3':9,10]cyclotetradeca[1,2-b]furan
InChi Key
OQGXDKRHMBRZCS-FLNKEUCVSA-N
InChi Code
InChI=1S/C20H30O2/c1-14-6-5-11-20(4)19(22-20)10-8-15(2)12-18-17(9-7-14)16(3)13-21-18/h6,12,18-19H,5,7-11,13H2,1-4H3/b14-6-,15-12+/t18-,19-,20-/m0/s1
SMILES Code
C/C1=C\[C@@H]2OCC(C)=C2CC/C(C)=C\CC[C@](C)(O3)[C@@H]3CC1
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
302.45
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: Nii K, Tagami K, Matsuoka K, Munakata T, Ooi T, Kusumi T. Unusual transannular cyclization products of sarcophytoxide, a 14-membered marine cembranoid: anomalous stereochemistry of epoxide-ketone rearrangement. Org Lett. 2006 Jul 6;8(14):2957-60. PubMed PMID: 16805526.
2: Cheng SY, Wang SK, Chiou SF, Hsu CH, Dai CF, Chiang MY, Duh CY. Cembranoids from the octocoral Sarcophyton ehrenbergi. J Nat Prod. 2010 Feb 26;73(2):197-203. doi: 10.1021/np900693r. PubMed PMID: 20099902.
3: Cheng SY, Wang SK, Hsieh MK, Duh CY. Polyoxygenated cembrane diterpenoids from the soft coral Sarcophyton ehrenbergi. Int J Mol Sci. 2015 Mar 17;16(3):6140-52. doi: 10.3390/ijms16036140. PubMed PMID: 25789502; PubMed Central PMCID: PMC4394524.
4: Grote D, Soliman HS, Shaker KH, Hamza M, Seifert K. Cembranoid diterpenes and a briarane diterpene from corals. Nat Prod Res. 2006 Mar;20(3):285-91. PubMed PMID: 16401561.
5: Matthée GF, König GM, Wright AD. Three new diterpenes from the marine soft coral Lobophytum crassum. J Nat Prod. 1998 Feb;61(2):237-40. PubMed PMID: 9548852.
6: Shaker KH, Müller M, Ghani MA, Dahse HM, Seifert K. Terpenes from the soft corals Litophyton arboreum and Sarcophyton ehrenbergi. Chem Biodivers. 2010 Aug;7(8):2007-15. doi: 10.1002/cbdv.201000016. PubMed PMID: 20730963.
7: Cuong NX, Tuan TA, Kiem PV, Minh CV, Choi EM, Kim YH. New cembranoid diterpenes from the Vietnamese soft coral Sarcophyton mililatensis stimulate osteoblastic differentiation in MC3T3-E1 cells. Chem Pharm Bull (Tokyo). 2008 Jul;56(7):988-92. PubMed PMID: 18591816.
8: Chen SH, Huang H, Guo YW. A new diterpenoid from the south China sea soft coral Lobophytum sp. J Asian Nat Prod Res. 2008 Sep-Oct;10(9-10):965-9. doi: 10.1080/10286020802217655. PubMed PMID: 19003616.
9: Shaaban M, Issa MY, Ghani MA, Hamed A, Abdelwahab AB. New pyranosyl cembranoid diterpenes from Sarcophyton trocheliophorum. Nat Prod Res. 2018 Feb 2:1-10. doi: 10.1080/14786419.2018.1431631. [Epub ahead of print] PubMed PMID: 29393673.
10: Januar HI, Zamani NP, Soedharma D, Chasanah E. New Cytotoxic Cembranoid from Indonesian Soft Coral Sarcophyton sp. Pharmacognosy Res. 2017 Jan-Mar;9(1):65-68. doi: 10.4103/0974-8490.199779. PubMed PMID: 28250656; PubMed Central PMCID: PMC5330105.