56324-31-3

Basic information

• Product Name: (+)-CUPARENE
• Synonyms: (+)-CUPARENE;CUPARENE, (+);(R)-1-(P-TOLYL)-1,2,2-TRIMETHYLCYCLOPENTANE;(-)-1-Methyl-4-[(S)-1,2,2-trimethylcyclopentyl]benzene;(S)-(-)-Cuparene;(S)-Cuparene;4-[(S)-1,2,2-Trimethylcyclopentane-1α-yl]toluene
• CAS NO: 56324-31-3
• Molecular Formula: C₁₅H₂₂
• Molecular Weight: 202.34
• EINECS: 241-061-5
• Mol File: 56324-31-3.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 275 °C(lit.)
• Appearance: /
• Density: 0.937 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.523
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-CUPARENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CUPARENE(56324-31-3)
• EPA Substance Registry System: (+)-CUPARENE(56324-31-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 56324-31-3(Hazardous Substances Data)

Usage

Description

(+)-CUPARENE is a naturally occurring sesquiterpene hydrocarbon found in various plant species, particularly in the Cupressaceae family. It is an organic compound derived from the isoprene unit and is known for its distinct sweet, woody aroma.
Used in Fragrance and Flavoring Industries:
(+)-CUPARENE is used as a fragrance and flavoring agent for its distinct sweet, woody aroma, making it a valuable component in the creation of perfumes, colognes, and food flavorings.
Used in Traditional Medicine:
(+)-CUPARENE is used as a medicinal agent for its potential anti-inflammatory and antioxidant properties, which may contribute to the treatment and prevention of various health conditions.
Used in Antimicrobial Applications:
(+)-CUPARENE is used as an antimicrobial agent for its potential to inhibit the growth of harmful microorganisms, making it a candidate for use in sanitizing products and medical applications.
Used in Insecticidal Applications:
(+)-CUPARENE is used as an insecticidal agent for its potential to deter or eliminate insects, which can be beneficial in agricultural and pest control settings.

Upstream product

• 470-40-6 thujopsene 
• 603137-30-0 3-Methyl-6-((S)-1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene 
• 54812-11-2 methyl 1,2,2-trimethylcyclopentanecarboxylate 
• 29606-94-8 (1S,3R)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid 
• 438626-01-8 1,2,2-trimethylcyclopentane-1-carboxaldehyde 
• 438626-00-7 1-hydroxymethyl-1,2,2-trimethylcyclopentane 
• 124-83-4 D-(+)-camphoric acid 
• 54846-69-4 (R)-1,2,2-trimethylcyclopent-3-enecarboxylic acid methyl ester 
• 15797-21-4 dimethyl (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate 
• 252264-89-4 ((R)-1,2,2-Trimethyl-cyclopent-3-enyl)-methanol 
• 252264-86-1 3-[(1R)-1,2,2-trimethylcyclopent-3-enyl]prop-2-enal 
• 252264-85-0 3-[(1R)-1,2,2-trimethylcyclopent-3-enyl]prop-2-enecarboxylic acid ethyl ester 
• 252285-40-8 (+)-3-hydroxycuparene 
• 252264-88-3 4-[(1R)-1,2,2-trimethylcyclopent-3-enyl]-3-hydroxybenzoic acid ethyl ester 

Downstream Products

• 934737-75-4 (R)-2-Nitro-cuparen 
• 509-02-4 Cuparensaeure 
• 38510-59-7 (R)-2-Acetoxycuparen 
• 52528-93-5 (R)-2-Benzoyloxycuparen 
• 52528-92-4 N-Acetyl-N-[2-methyl-5-((R)-1,2,2-trimethyl-cyclopentyl)-phenyl]-acetamide 

Relevant articles and documents

Catalytic asymmetric total syntheses of (+)-α-cuparenone, (+)-cuparene and (+)-herbertene

A general catalytic asymmetric route to either enantiomers of sesquiterpenes, cuparenes (1–2) and herbertenes (8–9) is disclosed from commercially available 3-methyl cyclopenten-2-one. Following a catalytic enantioselective addition of arylboronic acids to enone 15, compounds 14a-b with all carbon quaternary stereocenters are synthesized in up to 90percent ee in the presence of Pd(II)-PyOx (pyridine oxazoline). Compounds 14a-b are used as precursors for the asymmetric total syntheses of (+)-cuparene (1a) (35percent overall yield in 3 steps), α-(+)-cuparenone (1b) (56percent overall yield in 2 steps), and (+)-herbertene (8a) (34percent overall yield in 3 steps).

Stereospecific Construction of Contiguous Quaternary All-Carbon Centers by Oxidative Ring Contraction

Oxidative ring contraction of cyclic α-formyl ketones was facilitated by the action of H2O2under operationally simple and environmentally benign reaction conditions. The process was highly regioselective and enables stereospecific construction of contiguous quaternary all-carbon centers from stereodefined all-substituted all-cyclic ketones. The asymmetric syntheses of (+)-cuparene and (+)-tochuinyl acetate were also successively achieved by taking advantage of this novel protocol.

(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions

The title heterocyclic alcohol readily generates a sulfur-substituted allylic cation upon simple treatment with a protic acid, thus facilitating a synthetically useful stepwise (3+2) cycloaddition reaction pathway with a range of conjugated-olefin-type substrates. The introduction of an allyl fragment in this way provided rapid access to a variety of cyclopentanoid scaffolds. The cyclic nature of the cation precursor alcohol was shown to be instrumental for efficient cycloaddition reactions to take place, thus indicating an attractive strategy for controlling the reactivity of heteroatom-substituted allyl cations. The formal cycloaddition reaction is highly regio- and stereoselective and was also used for a short total synthesis of the natural product cuparene in racemic form through a cycloaddition–hydrodesulfurization sequence.