22422-34-0

Basic information

• Product Name: (1R,2R,3S,5R)-(-)-2,3-Pinanediol
• Synonyms: (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;(-)-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%
• CAS NO: 22422-34-0
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Product Categories: Chiral Compounds
• Mol File: 22422-34-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 101-102 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to very faint yellow/Liquid
• Density: 0.9409 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.4494 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol, Toluene
• PKA: 14.68±0.60(Predicted)
• BRN: 2039144
• CAS DataBase Reference: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(22422-34-0)
• EPA Substance Registry System: (1R,2R,3S,5R)-(-)-2,3-Pinanediol(22422-34-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 22422-34-0(Hazardous Substances Data)

Usage

Description

(1R,2R,3S,5R)-(-)-2,3-Pinanediol is a white crystalline solid that is a bicyclic monoterpene diol. It is a microbial oxidation product of (-)-β-pinene, which is a flavor and fragrance monoterpene. (1R,2R,3S,5R)-(-)-2,3-Pinanediol has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells, suggesting its potential for therapeutic applications and sunless tanning use.

Uses

Used in Pharmaceutical Applications:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol is used as a therapeutic agent for its ability to induce differentiation in certain types of cancer cells, such as S91 melanoma and PC12 pheochromocytoma cells. This property makes it a promising candidate for cancer treatment and research.
Used in Cosmetic Applications:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol is used as an ingredient in the cosmetic industry for its potential in sunless tanning. This application takes advantage of the compound's ability to induce cell differentiation, which could lead to a tanning effect without the need for exposure to sunlight or its associated risks.
Used in Flavor and Fragrance Industry:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol, being a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene, can be used as a component in the creation of various fragrances and flavors, leveraging its unique chemical properties to enhance or create new sensory experiences.

InChI:InChI=1/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+/m0/s1

Upstream product

• 7785-26-4 (-)-α-pinene 
• 22466-70-2 (1R,2S,5R)-6,6-dimethylspiro[bicycle[3.1.1]heptane-2,2’-oxiran]-3-one 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 60-29-7 diethyl ether 
• 80-56-8 Pinene 
• 7785-70-8 (+)-α-pinene 
• 80-56-8 rac-α-pinene 

Downstream Products

• 318993-93-0 (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol 
• 473-72-3 (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid 
• 500004-47-7 (E)-3-Phenyl-acrylic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester 
• 612835-98-0 (1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 948854-88-4 C₁₉H₂₅NO₄ 
• 852509-18-3 (-)-pinanediol (1S)-1-benzyloxy-3-[tert-butoxycarbonyl]propaneboronate 
• 852509-20-7 (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-chlorobutaneboronate 
• 852509-22-9 (-)-pinanediol (1R,2R)-2-benzyloxy-4-[tert-butoxycarbonyl]-1-vinylbutaneboronate 

Relevant articles and documents

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

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NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

A Modular Approach to the Asymmetric Synthesis of Cytisine

The asymmetric synthesis of (+)-and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.