Synonym
Dicranin; 9,12,15-Octadecatrien-6-ynoic acid
IUPAC/Chemical Name
9,12,15-Octadecatrien-6-ynoic acid
InChi Key
UXMMIMGEKFYPFK-IUQGRGSQSA-N
InChi Code
InChI=1S/C18H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+
SMILES Code
CC/C=C/C/C=C/C/C=C/CC#CCCCCC(O)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
274.40
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: Roy Chowdhuri S, Biswas Raha A, Mitra S, Datta J, Poddar Sarkar M. "Dicranin" in the Membrane Phospholipids of a Dicranaceae and Pottiaceae Moss Member of the Eastern Himalayan Biodiversity Hotspot. Lipids. 2018 May;53(5):539-545. doi: 10.1002/lipd.12054. Epub 2018 Aug 2. PMID: 30070366.
2: Mitra S. High Content of Dicranin in Anisothecium spirale (Mitt.) Broth., a Moss from Eastern Himalayas and Its Chemotaxonomic Significance. Lipids. 2017 Feb;52(2):173-178. doi: 10.1007/s11745-017-4231-8. Epub 2017 Jan 16. PMID: 28093643.
3: Borel C, Welti DH, Fernandez I, Colmenares M. Dicranin, an antimicrobial and 15-lipoxygenase inhibitor from the moss Dicranum scoparium. J Nat Prod. 1993 Jul;56(7):1071-7. doi: 10.1021/np50097a010. PMID: 8377015.
4: Guichardant M, Michel M, Borel C, Fay L, Magnolato D, Finot PA. Effects of 9, 12, 15-octadecatrien-6-ynoic acid on the metabolism of arachidonic acid in platelets and on platelet aggregation. Thromb Res. 1992 Mar 15;65(6):687-98. doi: 10.1016/0049-3848(92)90108-m. PMID: 1636161.
5: Rempt M, Schneider B, Pohnert G. A reactive conjugated allene involved in the biosynthesis of volatile oxylipins in the moss Dicranum scoparium. Org Lett. 2011 Jun 17;13(12):3229-31. doi: 10.1021/ol201114g. Epub 2011 May 23. PMID: 21604791.
6: Guichardant M, Michel M, Borel C, Fay L, Crozier G, Magnolato D, Finot PA. Effects of 9,12,15-octadecatrien-6-ynoic acid on the metabolism of arachidonic acid in platelets and on the platelet aggregation. Agents Actions Suppl. 1992;37:215-21. doi: 10.1007/978-3-0348-7262-1_30. PMID: 1632297.
7: Sperling P, Lee M, Girke T, Zähringer U, Stymne S, Heinz E. A bifunctional delta-fatty acyl acetylenase/desaturase from the moss Ceratodon purpureus. A new member of the cytochrome b5 superfamily. Eur J Biochem. 2000 Jun;267(12):3801-11. doi: 10.1046/j.1432-1327.2000.01418.x. PMID: 10848999.
