Synonym
(-)-Isopinocampheol; l-Isopinocampheol;
IUPAC/Chemical Name
(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol
InChi Key
REPVLJRCJUVQFA-BZNPZCIMSA-N
InChi Code
InChI=1S/C10H18O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-9,11H,4-5H2,1-3H3/t6-,7+,8-,9-/m1/s1
SMILES Code
O[C@H]1[C@H](C)[C@](C2)([H])C(C)(C)[C@]2([H])C1
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
154.25
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: Reller M, Wesp S, Koos MRM, Reggelin M, Luy B. Biphasic Liquid Crystal and the Simultaneous Measurement of Isotropic and Anisotropic Parameters by Spatially Resolved NMR Spectroscopy. Chemistry. 2017 Sep 27;23(54):13351-13359. doi: 10.1002/chem.201702126. Epub 2017 Jul 26. PubMed PMID: 28644550.
2: Hansmann S, Schmidts V, Thiele CM. Synthesis of Poly-γ-S-2-methylbutyl-l-glutamate and Poly-γ-S-2-methylbutyl-d-glutamate and Their Use as Enantiodiscriminating Alignment Media in NMR Spectroscopy. Chemistry. 2017 Jul 6;23(38):9114-9121. doi: 10.1002/chem.201700699. Epub 2017 Jun 20. PubMed PMID: 28370575.
3: Duporté G, Flaud PM, Geneste E, Augagneur S, Pangui E, Lamkaddam H, Gratien A, Doussin JF, Budzinski H, Villenave E, Perraudin E. Experimental Study of the Formation of Organosulfates from α-Pinene Oxidation. Part I: Product Identification, Formation Mechanisms and Effect of Relative Humidity. J Phys Chem A. 2016 Oct 13;120(40):7909-7923. Epub 2016 Sep 29. PubMed PMID: 27611844.
4: Krupp A, Reggelin M. Phenylalanine-based polyarylacetylenes as enantiomer-differentiating alignment media. Magn Reson Chem. 2012 Dec;50 Suppl 1:S45-52. doi: 10.1002/mrc.3894. PubMed PMID: 23280660.
5: Giraudeau P, Montag T, Charrier B, Thiele CM. Fast access to residual dipolar couplings by single-scan 2D NMR in oriented media. Magn Reson Chem. 2012 Dec;50 Suppl 1:S53-7. doi: 10.1002/mrc.3856. Epub 2012 Aug 5. Erratum in: Magn Reson Chem. 2013 Mar;51(3):192. PubMed PMID: 22865710.
6: Voskuhl J, Schaepe K, Ravoo BJ. Enhanced chiral recognition by cyclodextrin dimers. Int J Mol Sci. 2011;12(7):4637-46. doi: 10.3390/ijms12074637. Epub 2011 Jul 18. PubMed PMID: 21845101; PubMed Central PMCID: PMC3155374.
7: Marx A, Schmidts V, Thiele CM. How different are diastereomorphous orientations of enantiomers in the liquid crystalline phases of PBLG and PBDG: a case study. Magn Reson Chem. 2009 Sep;47(9):734-40. doi: 10.1002/mrc.2454. PubMed PMID: 19504463.
8: Paine JB 3rd. Esters of pyromellitic acid. Part II. Esters of chiral alcohols: para pyromellitate diesters as a novel class of resolving agents and use of pyromellitates as duplicands for chiral purification. J Org Chem. 2008 Jul 4;73(13):4939-48. doi: 10.1021/jo8005446. Epub 2008 Jun 4. PubMed PMID: 18522418.
9: de Sousa DP, Raphael E, Brocksom U, Brocksom TJ. Sedative effect of monoterpene alcohols in mice: a preliminary screening. Z Naturforsch C. 2007 Jul-Aug;62(7-8):563-6. PubMed PMID: 17913072.
10: Misra LN, Shawl AS, Raina VK. Volatile Constituents of Dracocephalum nutans. Planta Med. 1988 Apr;54(2):165-6. PubMed PMID: 17265231.
11: Suga T, Hirata T, Hamada H, Futatsugi M. Enantioselectivity in the biotransformation of bicyclic monoterpene alcohols with the cultured suspension cells of Nicotiana tabacum. Plant Cell Rep. 1983 Aug;2(4):186-8. doi: 10.1007/BF00270099. PubMed PMID: 24258047.
