IUPAC/Chemical Name
(1R,2S,5R,7R)-1,3,3-trimethyl-4,6-dioxatricyclo[3.3.1.02,7]nonane
InChi Key
SHTFZHTWSLHVEB-BDNRQGISSA-N
InChi Code
InChI=1S/C10H16O2/c1-9(2)8-6-4-10(8,3)5-7(11-6)12-9/h6-8H,4-5H2,1-3H3/t6-,7-,8+,10-/m1/s1
SMILES Code
CC1(C)[C@@]2([H])[C@](C3)(C)C[C@@]2([H])O[C@]3([H])O1
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
168.24
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: Salom SM, McLean JA. Flight and landing behavior ofTrypodendron lineatum (Coleoptera: Scolytidae) in response to different semiochemicals. J Chem Ecol. 1990 Aug;16(8):2589-604. doi: 10.1007/BF01017481. PubMed PMID: 24264223.
2: Shore TL, Lindgren BS. Effect of ethanol and α-pinene on response of ambrosia beetle,Trypodendron lineatum, to lineatin-baited funnel and drainpipe traps. J Chem Ecol. 1996 Dec;22(12):2187-96. doi: 10.1007/BF02029539. PubMed PMID: 24227296.
3: Alibés R, de March P, Figueredo M, Font J, Racamonde M, Parella T. Highly efficient and diastereoselective synthesis of (+)-lineatin. Org Lett. 2004 Apr 29;6(9):1449-52. PubMed PMID: 15101764.
4: Pérez L, Alibés R, de March P, Busqué F, Figueredo M, Font J. Stereodivergent synthesis of (+)- and (-)-isolineatin. J Org Chem. 2013 May 3;78(9):4483-9. doi: 10.1021/jo400487y. Epub 2013 Apr 22. PubMed PMID: 23581881.
5: Racamonde M, Alibés R, Figueredo M, Font J, de March P. Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin. J Org Chem. 2008 Aug 1;73(15):5944-52. doi: 10.1021/jo800970u. Epub 2008 Jul 8. PubMed PMID: 18605755.
6: Keeling CI, Ngo HT, Benusic KD, Slessor KN. Preparative chiral liquid chromatography for enantiomeric separation of pheromones. J Chem Ecol. 2001 Mar;27(3):487-97. PubMed PMID: 11441440.
7: Mori K. [Synthesis and biological activity of optically active insect pheromones]. Yakugaku Zasshi. 1982 Oct;102(10):899-910. Review. Japanese. PubMed PMID: 6762413.