ChemicalBook > CAS DataBase List > (1R,2R,3S,5R)-(-)-2,3-Pinanediol

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

Product Name
(1R,2R,3S,5R)-(-)-2,3-Pinanediol
CAS No.
22422-34-0
Chemical Name
(1R,2R,3S,5R)-(-)-2,3-Pinanediol
Synonyms
cis-α-Pinene Glycol;(-)-2-HYDROXYISOPINOCAMPHEOL;(1R,2R,3S,5R)-(-)-PINANEDIOL;(1R,2R,3S,5R)-2,3-PINANEDIOL;Bortezomib intermediate isomer;(1R,2R,3S,5R)-(-)-2,3-PINANEDIOL;(1R,2R,3S,5R)-(-)-Pinanediol 99%;(1R,2R,3S,5R)-(-)-2,3-Pinanediol,98%;(-)-(1R:2R:3S:5R)-cis-α-Pineneglycol;(1R,2R,3S,5R)-(-)-2,3-Pinanediol >
CBNumber
CB4208709
Molecular Formula
C10H18O2
Formula Weight
170.25
MOL File
22422-34-0.mol
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(1R,2R,3S,5R)-(-)-2,3-Pinanediol Property

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
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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
F 
10
HS Code 
29061990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
287784
Product name
(1R,2R,3S,5R)-(?)-Pinanediol
Purity
99%
Packaging
1g
Price
$59.16
Updated
2025/07/31
Sigma-Aldrich
Product number
287784
Product name
(1R,2R,3S,5R)-(?)-Pinanediol
Purity
99%
Packaging
5g
Price
$157
Updated
2025/07/31
TCI Chemical
Product number
P2245
Product name
(1R,2R,3S,5R)-(-)-2,3-Pinanediol
Purity
>98.0%(GC)
Packaging
1g
Price
$37
Updated
2025/07/31
TCI Chemical
Product number
P2245
Product name
(1R,2R,3S,5R)-(-)-2,3-Pinanediol
Purity
>98.0%(GC)
Packaging
5g
Price
$120
Updated
2025/07/31
TRC
Product number
P458400
Product name
(1R,2R,3S,5R)-(-)-2,3-Pinanediol
Packaging
1g
Price
$45
Updated
2021/12/16
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(1R,2R,3S,5R)-(-)-2,3-Pinanediol Chemical Properties,Usage,Production

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

7785-26-4

22422-34-0

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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(1R,2R,3S,5R)-(-)-2,3-Pinanediol Suppliers

Belgium 1 Canada 1 China 119 France 1 Germany 1 India 4 Japan 2 Switzerland 1 The Netherlands 1 United Kingdom 6 United States 22 USA 1 Global 160
Brunschwig chemie
Tel
--
Fax
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Email
brunschwig@brunschwig.nl
Country
The Netherlands
ProdList
4996
Advantage
67
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View Lastest Price from (1R,2R,3S,5R)-(-)-2,3-Pinanediol manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
(1R,2R,3S,5R)-(-)-2,3-Pinanediol 22422-34-0
Price
US $3.00-9.00/KG
Min. Order
0.1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2025-06-21
Henan Aochuang Chemical Co.,Ltd.
Product
(1R,2R,3S,5R)-(-)-2,3-Pinanediol 22422-34-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-27
Anhuyan (Hainan) Biotechnology Co., LTD
Product
(1R,2R,3S,5R)-(-)-2,3-Pinanediol 22422-34-0
Price
US $0.00/G/KG
Min. Order
1G/KG
Purity
99%
Supply Ability
10000000000KG
Release date
2025-02-12

22422-34-0, (1R,2R,3S,5R)-(-)-2,3-PinanediolRelated Search:

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

  • (-)-2-HYDROXYISOPINOCAMPHEOL
  • (1R,2R,3S,5R)-(-)-2,3-PINANEDIOL
  • (1R,2R,3S,5R)-2,3-PINANEDIOL
  • (1R,2R,3S,5R)-(-)-PINANEDIOL
  • [1R-(1ALPHA,2ALPHA,3ALPHA,5ALPHA)]-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTANE-2,3-DIOL
  • ((1R-(1ALPHA,2BETA,3BETA,5ALPHA))-2,6,6-TRIMETHYLBICYCLO(3.3.1)HEPTANE-2,3-DIOL)
  • (-)-2-Hydroxyisopinocampheol, [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol
  • (1R,2R,3S,5R)-(-)-2,3-Pinanediol,98%
  • [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol
  • Bortezomib intermediate isomer
  • (1R,2R,3S,5R)-(-)-2,3-Pinanediol ,99%
  • (-)-(1R:2R:3S:5R)-cis-α-Pineneglycol
  • (1R,2R,3S,5R)-2,6,6-TriMethylbicyclo[3.1.1]heptane-2,3-diol
  • [1R-(1α,2α,3α,5α)]-2,6,6-TriMethylbicyclo[
  • cis-α-Pinene Glycol
  • (1R,2R,3S,5R)-(-)-Pinanediol 99%
  • (1<i>R</i>,2<i>R</i>,3<i>S</i>,5<i>R</i>)-(-)-2,3-Pinanediol
  • (1R,2R,3S,5R)-(-)-2,3-Pinanediol &gt
  • Bicyclo[3.1.1]heptane-2,3-diol, 2,6,6-trimethyl-, (1R,2R,3S,5R)-
  • (1R,2R,3S,5R)-2,6,6-Trimethylnorpinane-2,3-diol
  • (1R,2R,3S,5R)-(-)-2,3-Pinanediol CAS NO.22422-34-0
  • (1<i>R</i>,2<i>R</i>,3<i>S</i>,5<i>R</i>)-(?)-Pinanediol
  • 22422-34-0
  • Polyols
  • Organic Building Blocks
  • Asymmetric Synthesis
  • Chiral Building Blocks
  • Chiral Compounds