(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

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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%

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

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

22422-34-0

Polyols

Organic Building Blocks

Asymmetric Synthesis

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