16982-00-6

Basic information

• Product Name: (+)-CUPARENE
• Synonyms: (+)-CUPARENE;CUPARENE, (+);(R)-Cuparene;1-Methyl-4-(1,2,2-trimethylcyclopentyl)benzene;2,2-trimethylcyclopentyl)-1-methyl-4-((theta)-benzen;Benzene, 1-methyl-4-(1,2,2-trimethylcyclopentyl)-, (R)-;Toluene, p-(1,2,2-trimethylcyclopentyl)-, (R)-(+)-;(R)-1-(P-TOLYL)-1,2,2-TRIMETHYLCYCLOPENTANE
• CAS NO: 16982-00-6
• Molecular Formula: C₁₅H₂₂
• Molecular Weight: 202.34
• EINECS: 241-061-5
• Mol File: 16982-00-6.mol

Chemical Properties

• Boiling Point: 275 °C(lit.)
• Flash Point: 110℃
• Appearance: /
• Density: 0.937 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0123mmHg at 25°C
• Refractive Index: n20/D 1.523
• Storage Temp.: 2-8°C
• BRN: 2326949
• CAS DataBase Reference: (+)-CUPARENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CUPARENE(16982-00-6)
• EPA Substance Registry System: (+)-CUPARENE(16982-00-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 16982-00-6(Hazardous Substances Data)

Usage

Uses

Used in Perfumery Industry:
(+)-Cuparene is used as a fragrance ingredient for its distinctive woody, spicy aroma, contributing to the unique scent profiles of perfumes and luxury products.
Used in Pharmaceutical Industry:
(+)-Cuparene is used as an anti-inflammatory agent for its ability to reduce inflammation, which can be beneficial in treating various inflammatory conditions.
(+)-Cuparene is used as an antimicrobial agent for its capacity to inhibit the growth of microorganisms, making it potentially useful in the development of new antibiotics and antiseptic products.
(+)-Cuparene is used as an analgesic for its pain-relieving properties, offering a natural alternative for managing mild to moderate pain.
Used in Insect Repellent Industry:
(+)-Cuparene is used as an insect repellent due to its potential to deter insects, providing a natural and eco-friendly solution for pest control.
Used in Cancer Research:
(+)-Cuparene is used as a potential anti-cancer agent in laboratory research, with its demonstrated effects on cancer cells indicating a possible role in the development of new cancer therapies.

InChI:InChI=1/C15H22/c1-12-6-8-13(9-7-12)15(4)11-5-10-14(15,2)3/h6-9H,5,10-11H2,1-4H3/t15-/m0/s1

Upstream product

• 252264-85-0 3-[(1R)-1,2,2-trimethylcyclopent-3-enyl]prop-2-enecarboxylic acid ethyl ester 
• 252264-86-1 3-[(1R)-1,2,2-trimethylcyclopent-3-enyl]prop-2-enal 
• 252264-89-4 ((R)-1,2,2-Trimethyl-cyclopent-3-enyl)-methanol 
• 15797-21-4 dimethyl (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate 
• 54846-69-4 (R)-1,2,2-trimethylcyclopent-3-enecarboxylic acid methyl ester 
• 124-83-4 D-(+)-camphoric acid 
• 438626-00-7 1-hydroxymethyl-1,2,2-trimethylcyclopentane 
• 438626-01-8 1,2,2-trimethylcyclopentane-1-carboxaldehyde 
• 29606-94-8 (1S,3R)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid 
• 54812-11-2 methyl 1,2,2-trimethylcyclopentanecarboxylate 
• 603137-30-0 3-Methyl-6-((S)-1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene 
• 470-40-6 thujopsene 
• 93164-09-1 α,α,β-Trimethyl-β-p-tolyl-adipinsaeure 
• 108-40-7 toluene-3-thiol 

Downstream Products

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

Relevant articles and documents

New Cuparene-Derived Sesquiterpenes with Unprecedented Oxygenation Patterns from the Sea Hare Aplysia dactylomela

Five new sesquiterpenes, cyclolaurene (2), cyclolaurenol (3), cyclolaurenol acetate (4), cupalaurenol (5), and cupalaurenol acetate (6), were isolated from the sea hare Aplysia dactylomela.Their structures including absolute configurations were deduced from spectroscopic data and chemical interconversion.The terpenes 3-6 are the first examples in which bromine and hydroxyl or acetoxy substituents are reversed in their positions from those usually found in related compounds, e.g., laurinterol (1).

ENANTIOMERIC TYPE SESQUITERPENOIDS OF THE LIVERWORT MARCHANTIA POLYMORPHA

Marchantia Polymorpha; Hepaticae; Bryophyte; biogenesis; ent-type sesquiterpenoids; optical antipodes; new compounds.A series of ent-sesquiterpenoids corresponding to the optical antipodes of those in higher plants have been isolated from the liverwort Marchantia polymorpha.These sesquiterpenoids provide yet another example of the peculiar stereospecificity of the biogenesis of the liverwort sesquiterpenoids and suggest a special taxonomic position of the liverworts in the plant kingdom.

Synthesis of cuparene and herbertene via a common intermediate

A dihydroisobenzofuran (13) was obtained from β-ionone in 10 steps via an intramolecular Diels-Alder reaction. On further oxidation, reductive ring opening and decarboxylation, cuparene and'herbertene were synthesized.

Use of aromatic radical-anions in the absence of THF. Tandem formation and cyclization of benzyllithiums derived from the attack of homo- and bishomoallyllithiums on α-methylstyrenes: Two-pot synthesis of cuparene

When a homo- or bishomoallyllithium, generated by reductive lithiation of the corresponding phenyl thioether by the radical anion lithium 1-(dimethylamino)naphthalenide (LDMAN), is added to α-methylstyrene, a tandem addition/cyclization to a phenyl-substituted five- or six-membered-ring occurs. The yields are compromised by polymerization of the α-methylstyrene, a process favored by tetrahydrofuran (THF), the solvent used to generate lithium aromatic radical anions. Thus, a new method of generating LDMAN (unsuccessful for other common radical anions) in the absence of THF has been developed. The radical anion can be generated and the reductive lithiation performed in dimethyl ether at -70 °C. After the addition of diethyl ether or other solvent, and evaporation of the dimethyl ether in vacuo, the α-methylstyrene is added and the solution is warmed to -30 °C. When the unsaturated alkyllithium is primary, no adduct forms in THF due to polymerization of the α-methylstyrene, but moderate yields are attained in a solvent containing mainly hexanes. It was also found that the cyclized organolithiums, which would have become protonated in the presence of THF, can be captured by an electrophile, even at ambient temperature. A two-pot synthesis, the most efficient reported, of the sesquiterpene (±)-cuparene in 46% yield, using this technology is reported.

A Short Synthesis of (+/-)-Cuparene

Lewis-acid-promoted reaction of m-tolylthiomethyl chloride (1) with 1,2-dimethylcyclopentene (2) followed by desulphurisation of the resultant + + 2> cycloadduct (4) gives (+/-)-cuparene (5).

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).

New Strategy for Forging Contiguous Quaternary Carbon Centers via H 2 O 2 -Mediated Ring Contraction

Stereospecific construction of contiguous quaternary carbon centers constitutes a major challenge in natural product synthesis. A general protocol that enables stereospecific construction of all stereoisomers of such a moiety remains elusive. In this article, we will discuss the oxidative ring contraction of all-substituted cyclic α-formyl ketones mediated by H 2 O 2, which provides a facile access to the stereospecific construction of contiguous quaternary carbon centers.

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.

RCM-based approach to (±)-cuparene

An efficient approach to the aromatic sesquiterpene cuparene has been described starting from the readily available β-ionone and employing a combination of epoxide rearrangement-based ring-contraction and ring-closing metathesis reactions as key steps. Copyright Taylor & Francis Group, LLC.