3-CARENE

Description

Hydroperoxides of Δ-3-carene are allergens contained in turpentine. Occupational exposure occurs in painters, varnishers, or in ceramic decoration. The percentage of Δ-3-Carene is higher in Indonesian turpentine than in Portugese.

Description

(±)-3-Carene is a bicyclic monoterpene found in a variety of plants, including Cannabis. It decreases phagocytosis by rat alveolar macrophages when used at a concentration of 0.5 μM and decreases their viability at a concentration of 5 μM. (±)-3-Carene increases the expression and activity of alkaline phosphatase in mouse osteoblastic MC3T3-E1 subclone 4 cells, indicating induction of osteoblastic differentiation. It also induces calcium formation and increases the expression of osteopontin and type I collagen, which are related to osteoblast mineralization. (±)-3-Carene induces bronchoconstriction in isolated guinea pig lungs when exposed at an air concentration of 3,000 mg/m³.

Chemical properties

Clear, colorless liquid. Stable to approx- imately 250C, resinifies with oxygen. Insoluble in water; miscible with organic solutions. Com- bustible.

Chemical properties

3-Carene has a sweet, pungent turpentine-like taste.

Occurrence

Reported present in basil oil, bell pepper, bilberry, black currant berry juice and buds, fennel oil, grapefruit juice, kumquat peel oil, lemon peel oil, lime peel oil (cold pressed and distilled), lovage seed, mandarin peel oil, orange juice, orange peel oil, orange (bitter) peel oil, tangerine peel oil and other natural products.

The Uses of 3-CARENE

Solvent, intermediate. 3-Carene is a mutagenic compound that may be found in the fumes of heating freshly cut spruce and birch chips. 3-Carene is also found i many esential oils and it inhibits acetylcholinesterase activity.

What are the applications of Application

3-Carene is a bicyclic monoterpene turpentine constituent

Definition

A terpene hydrocarbon with both a 6-member and 3-member ring.

Preparation

Extracted from the pine tree oil.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 5255, 1984 DOI: 10.1016/S0040-4039(01)81577-X

General Description

Colorless liquid with a sweet, turpentine-like odor. Floats on water.

Reactivity Profile

3-CARENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Will attack some forms of plastics [USCG, 1999].

Health Hazard

Inhalation causes headache, confusion, respiratory distress. Ingestion irritates entire digestive system and may injure kidneys; if liquid enters lungs, it causes severe pneumonitis. Contact with eyes or skin causes irritation.

Contact allergens

Hydroperoxides of D-3-carene are allergens contained in turpentine. Occupational exposure occurs in painters, varnishers, or ceramic decoration. The percentage of D-3-carene is higher in Indonesian than in Portuguese turpentine.