18172-67-3

Basic information

• Product Name: (1S)-(1)-beta-Pinene
• Synonyms: (1S)-(-)-pin-2(10)-ene;2(10)-Pinene, (1S,5S)-(-)-;6,6-dimethyl-2-methylene-,(1S)-Bicyclo[3.1.1]heptane;6-dimethyl-2-methylene-(1s)-bicyclo[3.1.1]heptan;PINENE BETA;PINENE, (1S)-(-)-B-;(1s)-(1)-beta-pinene;(1S)-(-)-B-PINENE
• CAS NO: 18172-67-3
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 242-060-2
• Product Categories: Industrial/Fine Chemicals
• Mol File: 18172-67-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: −61 °C(lit.)
• Boiling Point: 165-167 °C(lit.)
• Flash Point: 91 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.866 g/mL at 25 °C
• Vapor Density: 4.7 (vs air)
• Vapor Pressure: ~2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.478
• Storage Temp.: 2-8°C
• Solubility: 95% ethanol: soluble1ml/3ml, clear, colorless
• Water Solubility: insoluble
• Merck: 14,7446
• BRN: 2038282
• CAS DataBase Reference: (1S)-(1)-beta-Pinene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(1)-beta-Pinene(18172-67-3)
• EPA Substance Registry System: (1S)-(1)-beta-Pinene(18172-67-3)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 10-20/21/22-36/37/38-43-51-65-51/53-50
• Safety Statements: 16-26-36/37-46-61-62
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• RTECS: DT5077000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 18172-67-3(Hazardous Substances Data)

Usage

Description

(1S)-(1)-beta-Pinene, also known as (-)-β-Pinene, is a bicyclic monoterpene found in various plants, including C. sativa. It exhibits diverse biological activities and has a clear colorless to pale yellow liquid appearance.

Uses

Used in Proteomics Research:
(1S)-(1)-beta-Pinene is used as a biochemical for proteomics research, aiding in the study of proteins and their interactions within biological systems.
Used in Natural Product Preparation:
(1S)-(1)-beta-Pinene is employed in the preparation of natural products such as grandisol and robustadial, contributing to the synthesis of valuable compounds derived from plant sources.
Used as a Perfuming Agent in the Cosmetics Industry:
(1S)-(1)-beta-Pinene is applied as a perfuming agent in the cosmetics industry, utilizing its natural aroma to enhance the scent of various products.
Used in Terpenoid Compound Analysis:
(-)-β-Pinene serves as a standard for the analysis of terpenoid compounds in plant essential oils by gas chromatography (GC) analysis, ensuring accurate identification and quantification of these compounds.
Used as a Building Block for Natural Product Synthesis:
(-)-β-Pinene may be used as a building block to synthesize natural products such as grandisol, robustadial, and (+)-nopinone, playing a crucial role in the creation of valuable plant-derived compounds.
Used in Hydroformylation Reactions:
(-)-β-Pinene undergoes hydroformylation in the presence of platinum/tin catalysts to form trans-10-formylpinane, a process that contributes to the synthesis of various chemical compounds.

InChI:InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8?,9-/m0/s1

Upstream product

• 7785-26-4 (-)-α-pinene 
• 763-10-0 geranyl diphosphate 
• 18448-88-9 2-crotylphenol 
• 471-10-3 linalyl chloride 
• 55527-89-4 (-)-myrtenyl bromide 
• 19894-97-4 (1R)-Myrtenol 
• 177698-19-0 Beta-pinene 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 547-61-5 pinocarveol 
• 22321-84-2 pinocarveyl hydroperoxide 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 367262-86-0 C₃₂H₃₆N₂O 
• 367262-89-3 C₃₂H₃₆N₂O₂ 

Downstream Products

• 53254-54-9 (R)-((1R)-pin-2-en-10-yl)-succinic acid-anhydride 
• 19876-54-1 (4S)-1-(2,2,2-trichloroethyl)-4-(2-chloroisopropyl)cyclohex-1-ene 
• 464-45-9 endo-borneol 
• 35836-73-8 (1R)-(-)-nopol 
• 35836-72-7 nopyl acetate 
• 138-86-3 limonene. 
• 6931-54-0 β-pinene oxide 
• 56246-58-3 β-pinene oxide 
• 80-56-8 Pinene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 532-87-6 p-camphorene 
• 5989-54-8 (-)-(S)-limonene 
• 3016-19-1 (E,E)-2,6-dimethyl-2,4,6-octatriene 
• 4755-33-3 pinane 

Relevant articles and documents

Isotopically Sensitive Branching as a Tool for Evaluating Multiple Product Formation by Monoterpene Cyclases

The deuterated substrates geranyl pyrophosphate and geranyl pyrophosphate were employed to examine isotopically sensitive branching in the biosynthesis of monoterpene olefin isomers.By this method, (-)-α-pinene and (-)-β-pinene were shown to be synthesized via a common intermediate by a single cyclization enzyme from grand fir (Abies grandis), as were (-)-α-phellandrene and (-)-β-phellandrene by a single cyclase from lodgepole pine (Pinus contorta).Kinetic isotope effects were determined for the various deprotonations leading to the pinenes and phellandrenes.Key Words: Isotopically sensitive branching, monoterpene biosynthesis, monoterpene cyclase, resin biosynthesis, kinetic isotope effect.

Acorenone B: AChE and BChE inhibitor as a major compound of the essential oil distilled from the ecuadorian species niphogeton dissecta (Benth.) J.F. macbr

This study investigated the chemical composition, physical proprieties, biological activity, and enantiomeric analysis of the essential oil from the aerial parts of Niphogeton dissecta (culantrillo del cerro) from Ecuador, obtained by steam distillation. The qualitative and quantitative analysis of the essential oil was realized by gas chromatographic and spectroscopic techniques (GC-MS and GC-FID). Acorenone B was identified by GC-MS and NMR experiments. The enantiomeric distribution of some constituents has been assessed by enantio-GC through the use of a chiral cyclodextrin-based capillary column. We identified 41 components that accounted for 96.46% of the total analyzed, the major components were acorenone B (41.01%) and (E)-β-ocimene (29.64%). The enantiomeric ratio of (+)/(-)-β-pinene was 86.9:13.1, while the one of (+)/(-)-sabinene was 80.9:19.1. The essential oil showed a weak inhibitory activity, expressed as Minimal Inhibitory Concentration (MIC), against Enterococcus faecalis (MIC 10 mg/mL) and Staphylococcus aureus (MIC 5 mg/mL). Furthermore, it inhibited butyrylcholinesterase with an IC50 value of 11.5 μg/mL. Pure acorenone B showed inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, with IC50 values of 40.8 μg/mL and 10.9 μg/mL, respectively.

The first regio- and diastereoselective synthesis of homochiral perhydroimidazoisoxazoles via the 1,3-dipolar cycloaddition of imidazoline 3-oxides with (1S)-(-)-β-pinene

The 1,3-dipolar cycloaddition of imidazoline 3-oxides 1 with (1S)-(-)-β-pinene proceeds regio- and diastereoselectively to give homochiral perhydroimidazoisoxazole derivatives 3 in high yields in the cases of imidazoline 3-oxides 1a-e but in low yields in