1845-25-6

Basic information

• Product Name: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone
• Synonyms: (1S,2S,5S)-(-)-2-HYDROXY-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-3-ONE;(1S,2S,5S)-2-HYDROXY-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPTAN-3-ONE;(-)-(1S,2S,5S)-2-HYDROXY-3-PINANONE;(1S,2S,5S)-(-)-2-HYDROXY-3-PINANONE;(1S,2S,5S)-(-)-2-HYDROXYPINAN-3-ONE;Hydroxypinanone; (-)-2a-Hydroxypinocamphone;(1S 2S 5S)-(-)-2-HYDROXYPINAN-3-ONE 99+%
• CAS NO: 1845-25-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• Product Categories: Chiral Reagents;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Synthetic Organic Chemistry;Terpenes;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1845-25-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 36-38 °C(lit.)
• Boiling Point: 245 °C(lit.)
• Flash Point: 224 °F
• Appearance: /
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00491mmHg at 25°C
• Refractive Index: -33 ° (C=0.5, CHCl3)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate, Methanol
• PKA: 12.93±0.40(Predicted)
• BRN: 3196635
• CAS DataBase Reference: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(1845-25-6)
• EPA Substance Registry System: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(1845-25-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1845-25-6(Hazardous Substances Data)

Usage

Description

(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is a chiral auxiliary used in the synthesis of various compounds and is also found as an essential oil in Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult. It is a white solid with unique chemical properties.

Uses

Used in Synthesis:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is used as a chiral auxiliary for the synthesis of various compounds, providing a stereoselective approach to the formation of complex molecules.
Used in Cosmetics:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is used as an essential oil in cosmetics for its unique fragrance and potential benefits to the skin.
Used in the Production of Essential Oils:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is found in the essential oils of Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult., which are used in various applications such as aromatherapy and perfumery.

InChI:InChI=1/C10H16O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-7,12H,4-5H2,1-3H3/t6?,7?,10-/m0/s1

Upstream product

• 80-56-8 rac-α-pinene 
• 7785-70-8 (+)-α-pinene 
• 67617-36-1 2α-hydroxy-2,6,6-trimethybicyclo<3.1.1>heptan-3-one oxime 
• 18680-27-8 pinanediol 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 7785-26-4 (-)-α-pinene 
• 176896-75-6 tert-butyl 2-[(E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino]acetate 
• 21803-49-6 (1S,2S,3R,5S)-(+)-pinanediol 
• 80-56-8 Pinene 
• 329710-76-1 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate 
• 473-62-1 (1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one 
• 14575-93-0 isopinocamphone 
• 276253-82-8 tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 918625-33-9 (2S)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol 
• 918625-33-9 (2R)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol 
• 125423-99-6 [(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid cyclohexyl ester 
• 125423-98-5 [(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 125423-98-5 [(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 90473-00-0 ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C 
• 126003-96-1 (1S,2S,5S)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 18680-27-8 pinanediol 
• 328000-43-7 (1S,2S,5S)-3-(4,5-Diphenyl-1,3-oxazol-2-ylmethylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 112091-01-7 8-hydroxy-6-p-menthen-2-one oxime 
• 134101-89-6 8-isobutyrylamino-p-menth-6-en-2-one oxime 

Relevant articles and documents

New optically active cn-palladacycles based on 2α-hydroxypinan-3-one and camphor derivatives

The ligand (-)-2α-hydroxypinan-3-one diphenylmethylimine was synthesized and studied. New dinuclear CN-palladacycles and their mononuclear triphenylphosphine derivatives were obtained. It was shown that ortho-palladation of terpene diphenylmethylimines pr

New unsymmetrical salen-type ligand from enantiomerically pure 2-hydroxypinan-3-one

The reaction of enantiomerically pure (-)-2-hydroxypinan-3-one with ethylenediamine was studied. Depending on the reagent ratio, the reaction can afford either mono- or bis-Schiff's bases. The enantiomerically pure unsymmetrical terpenoid salen-type ligan

Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one

Seven novel palladium complexes of the type [Pd(HL)Cl2] and [Pd(L)Cl] containing chiral pinane ligands (HL = 3-[(2-aminoethyl)imino]-pinane-2-ol; 3,3′-(ethylenediimino)bis-pinane-2-ol; cis-3-(2-aminoethylamino)-pinane-2-ol; cis-3,3′(ethylenediamino)bis-pinane-2-ol; trans-3,3′(ethylenediamino)bis-pinane-2-ol; 3-[2-(2-hydroxybenzylamino)ethylamino]-pinane-2-ol; L = 3-[2-(3,5-di-tert-butyl-2-hydroxybenzylidene)aminoethylimino]pinane-2-ol) were synthesized in good yields from the direct reaction of chiral nitrogen ligands with Li2PdCl4 in MeOH. These synthesized complexes were characterized by means of elemental analysis, FT-IR, multidimensional and multinuclear NMR spectroscopic methods.

Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid-a CF3O-containing analogue of natural lipophilic amino acids

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes

In this study, we synthesized five new chiral ligands from (+) and (-)-α-pinene, which were successfully employed in the stereoselective addition of diethylzinc to aldehydes, leading to secondary chiral alcohols in up to 99% yield and 94% e.e.