Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H18O2 |
| Molecular Weight | 170.2487 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)[C@@H](O)C2
InChI
InChIKey=MOILFCKRQFQVFS-BDNRQGISSA-N
InChI=1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m1/s1
Equimolar mixture of the BMTd's 2,3-cis/exo-pinanediol (Pinanediol) and 2,3-cis/exo-camphanediol stimulates nitric oxide synthesis in epithelial cells of the skin, specifically normal human epidermal keratinocytes (NHEK) and normal human microvascular endothelial cells (HMVEC). Pinanediol is an effective inducer of melanogenesis. It induces differentiation of S91 melanoma and PC12 pheochromocytoma cells by a cyclic guanosine-monophosphate-dependent pathway.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates. | 2010-01-15 |
|
| Direct chemical synthesis of chiral methanol of 98% ee and its conversion to [(2)H1,(3)H]methyl tosylate and [(2)H1,(3)H-methyl]methionine. | 2005-10-12 |
Patents
Sample Use Guides
Guinea pigs:The amount of pigmentation induced in guinea pig
skin by 1 M 2,3-cis/exo-pinanediol (Pinanediol) in 50% ETOH was
equal to that induced by 8.7 M 1,2-cs-CPD in 20% ETOH.
Route of Administration:
Topical
In Vitro Use Guide
Curator's Comment: 2,3-cis/exo-pinanediol (Pinanediol) induced more tyrosinase in S91 cells
than 5-NBene-2,2-DM at all concentrations tested between 100 uM and 2.5 mM. Approximately 100-fold induction of tyrosinase occurred at 2.5 mM
2,3-cis/exo-pinanediol and 5 mM 5-NBene-2,2-DM. The lowest concentration of either compound that resulted in significant induction of tyrosinase was
100 uM. https://www.ncbi.nlm.nih.gov/pubmed/10193680
Equimolar mixture of the BMTd's 2,3-cis/exo-pinanediol (Pinanediol) and 2,3-cis/exo-camphanediol stimulates nitric oxide synthesis in epithelial cells of the skin, specifically normal human epidermal keratinocytes (NHEK) and normal human microvascular endothelial cells (HMVEC). A 1 mM mixture increased nitric oxide 3-fold in HMVEC in the first 24 h after treatment, and a 2 mM mixture produced an equivalent increase in NHEK.
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SUBSTANCE RECORD
