(1R,2R,3S,5R)-(-)-2,3-Pinanediol Chemical Properties

Melting point:

57-59 °C(lit.)

alpha 

-8.5 º (c=6.5, toluene)

Boiling point:

101-102 °C1 mm Hg(lit.)

Density 

0.9409 (rough estimate)

refractive index 

1.4494 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol, Toluene

pka

14.68±0.60(Predicted)

form 

Liquid

color 

Clear colorless to very faint yellow

optical activity

[α]21/D 8.6°, c = 6.5 in toluene

BRN 

2039144

Cosmetics Ingredients Functions

SKIN CONDITIONING

InChI

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

InChIKey

MOILFCKRQFQVFS-BDNRQGISSA-N

SMILES

[C@@]12([H])C[C@@]([H])(C1(C)C)C[C@H](O)[C@]2(C)O

LogP

1.582 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

F 

10

HS Code 

29061990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(1R,2R,3S,5R)-(-)-2,3-Pinanediol Usage And Synthesis

Chemical Properties

white crystalline solid

Uses

(1R,2R,3S,5R)-(-)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene.

Synthesis

Under nitrogen protection, (-)-α-pinene (15 mL, 97 mmol) was dissolved in 100 mL of tert-butanol with Me3NO-2H2O (11 g, 102 mmol). Pyridine (7 mL) and osmium tetroxide (51 mg, 0.2 mmol) were added sequentially and heated to reflux. After 20 hours of reaction, the completion of the reaction was confirmed by TLC monitoring. The reaction mixture was cooled to room temperature, NaHSO3 (1.2 g, 12 mmol) was added and stirred for 1 hour. The reaction solution was transferred to a partition funnel and the organic phase was separated. The aqueous phase was extracted with ether (3 x 20 mL), the organic phases were combined and dried with anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporator. The product was purified by column chromatography (petroleum ether:ethyl acetate=30:1) to give 14 g of white solid in 85% yield.

References

[1] Patent: CN107151255, 2017, A. Location in patent: Paragraph 0176; 0177; 0178
[2] Helvetica Chimica Acta, 1987, vol. 70, p. 954 - 974
[3] Synthesis, 2003, # 13, p. 2053 - 2056
[4] Journal of Organic Chemistry, 1971, vol. 36, p. 2319,2322
[5] Australian Journal of Chemistry, 1974, vol. 27, p. 2199 - 2204

(1R,2R,3S,5R)-(-)-2,3-Pinanediol(22422-34-0)Related Product Information

• Sodium 1-heptanesulfonate
• 1-Methoxy-2-propyl acetate
• Ethylene glycol
• (S,S)-2,3-Butanediol
• Heptane
• Polyethylene Glycol
• 2-Butoxyethanol
• Estradiol
• Propylene glycol
• 2,2-Dimethyl-1,3-propanediol
• TETRAHYDROLINALOOL
• (1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL
• 3,3-DIMETHYL-1-BUTANOL
• Cyclobutanemethanol
• 1,2-Cyclohexanediol
• 2,5-DIMETHYLCYCLOHEXANOL
• (1R)-(+)-TRANS-PINANE
• 3,5-DIMETHYL-3-HEPTANOL