Synonym
Laserpitin; NSC-109434; NSC 109434; NSC109434;
IUPAC/Chemical Name
(1S,3aR,4R,6S,8R)-1,6-dihydroxy-1-isopropyl-3a,6-dimethyl-5-oxodecahydroazulene-4,8-diyl (2E,2'E)-bis(2-methylbut-2-enoate)
InChi Key
LYTPVRMVQVQYGM-JQESTGSSSA-N
InChi Code
InChI=1S/C25H38O7/c1-9-15(5)21(27)31-17-13-24(8,29)19(26)20(32-22(28)16(6)10-2)23(7)11-12-25(30,14(3)4)18(17)23/h9-10,14,17-18,20,29-30H,11-13H2,1-8H3/b15-9+,16-10+/t17-,18?,20+,23-,24+,25+/m1/s1
SMILES Code
O=C1[C@H](OC(/C(C)=C/C)=O)[C@]2(C)CC[C@@](C(C)C)(O)C2[C@H](OC(/C(C)=C/C)=O)C[C@@]1(O)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
450.57
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: Ogawa H, Nakamura R, Baba K. Beneficial effect of laserpitin, a coumarin compound from Angelica keiskei, on lipid metabolism in stroke-prone spontaneously hypertensive rats. Clin Exp Pharmacol Physiol. 2005 Dec;32(12):1104-9. PubMed PMID: 16445577.
2: Shehzad O, Khan S, Ha IJ, Park Y, Tosun A, Kim YS. Application of stepwise gradients in counter-current chromatography: a rapid and economical strategy for the one-step separation of eight coumarins from Seseli resinosum. J Chromatogr A. 2013 Oct 4;1310:66-73. doi: 10.1016/j.chroma.2013.08.033. Epub 2013 Aug 16. PubMed PMID: 23992840.
3: Mohammadi M, Yousefi M, Habibi Z, Shafiee A. Two new coumarins from the chloroform extract of Angelica urumiensis from Iran. Chem Pharm Bull (Tokyo). 2010 Apr;58(4):546-8. PubMed PMID: 20410639.
4: Tosun A, Akkol EK, Yeşilada E. Anti-inflammatory and antinociceptive activity of coumarins from Seseli gummiferum subsp. corymbosum (Apiaceae). Z Naturforsch C. 2009 Jan-Feb;64(1-2):56-62. PubMed PMID: 19323267.
5: Popović V, Goeman J, Thommis J, Heyerick A, Caroen J, Van der Eycken J, De Bosscher K. Daucane esters from laserwort (Laserpitium latifolium L.) inhibit cytokine and chemokine production in human lung epithelial cells. Phytomedicine. 2017 Mar 15;26:28-36. doi: 10.1016/j.phymed.2017.01.001. Epub 2017 Jan 5. PubMed PMID: 28257662.
6: Popović V, Goeman JL, Bougarne N, Eyckerman S, Heyerick A, De Bosscher K, Van der Eycken J. Involvement of the Glucocorticoid Receptor in Pro-inflammatory Transcription Factor Inhibition by Daucane Esters from Laserpitium zernyi. J Nat Prod. 2017 May 26;80(5):1505-1513. doi: 10.1021/acs.jnatprod.7b00012. Epub 2017 May 10. PubMed PMID: 28489375.
