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

• 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 
• 125423-98-5 [(1R,2R,5R)-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 [(1R,2R,5R)-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 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 
• 126003-96-1 (1S,2S,5S)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 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 
• 328000-60-8 (1R,2R,5R)-3-(4,5-Diphenyl-1,3-oxazol-2-ylmethylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

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

Chiral Titanium(IV) Complexes Containing Polydentate Ligands Based on α-Pinene. Catalytic Activity in Sulfoxidation with Hydrogen Peroxide

The reaction of TiCl4-n(OiPr)n (n = 0, 2, 4) with various terpenoid preligands based on α-pinene, C7H6Me3(OH)(NCH2CH2G) (G = NH2, I; NHMe, II; OH, III), stereoselectively affords a series of new chiral titanium(IV) complexes. Such complexes are either octahedral, [TiCl2X(OC7H6Me3NCH2CH2G-κ3N,N,O)] (X = Cl, G = NH2, 1; X = OiPr, G = NH2, 2; G = NHMe, 3), or trigonal bipyramidal, [Ti(OiPr)3(OC7H6Me3NCH2CH2G-κ2N,O)] (G = NH2, 4; NHMe, 5) and [TiX(OiPr)(OC7H6Me3NCH2CH2O-κ3N,O,O?)] (X = Cl, 6; OiPr, 8), depending on the acidity of titanium, the reaction conditions and the nature of the pendant ending group of the terpenoid ligand. Density functional theory (DFT) calculations have been carried out to assess the stability of the multiple possible diastereoisomers allowing us to propose structural suggestions. The new titanium complexes efficiently catalyze the selective oxidation of various types of sulfides to either sulfoxides or sulfones using aqueous hydrogen peroxide, under mild conditions. All compounds have been characterized by multinuclear NMR spectroscopy and the molecular structure for some of them has been determined by X-ray diffraction.

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.