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.

Synthetic method of chiral vicinal diol and product thereof

The invention provides a synthetic method of chiral vicinal diol, which comprises the following steps: (1) adding alkene used as a precursor of the chiral vicinal diol and dichloromethane into a reaction device, adding alkali, and then at a temperature of minus 50 DEG C to minus 15 DEG C, adding a phase-transfer catalyst and then adding potassium permanganate or sodium permanganate in batches to perform a reaction so as to obtain an intermediate a; (2) adding the intermediate a into the reaction device, adding ethyl ether and petroleum ether with stirring, then adding boric acid in batches, and dropwise adding aqueous solution of potassium hydroxide to perform a reaction so as to obtain an intermediate b; (3) adding the intermediate b into the reaction device, adding ethyl ether and water, and then under the ice bath cooling condition, dropwise adding hydrofluoric acid, and stirring overnight at a low temperature to obtain the chiral vicinal diol. According to the synthetic method provided by the invention, the potassium permanganate or the sodium permanganate which is cheap, has low toxicity and pollutes the environment a little is used as a reaction reagent, and industrial synthetic production of a chiral vicinal diol compound is achieved.