7445. α-Pinene

Nomenclature

CAS number: 80-56-8
2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; 2-pinene; pinene.
C10H16; mol wt 136.23.
C 88.16%, H 11.84%.

Description and references

Obtained from oil of turpentine which contains 58-65% α-pinene along with 30% β-pinene, q.v.: E. Gildemeister, F. Hoffmann, Die "atherischen Ole Band IV (Akademie-Verlag, Berlin, 4th ed., 1956) p 39. α-Pinene in North American oils is dextrorotatory, in most European oils it is levorotatory. Constituent of many volatile oils. Isoln of d-α-pinene from Port Oxford cedar wood oil (Chamaecyparis lawsoniana Parl., Pinaceae): Thurber, Roll, Ind. Eng. Chem. 19, 739 (1927). Isoln of l-α-pinene from mandarin peel oil (Citrus reticulata Blando, Rutaceae): Kugler, Kováts, Helv. Chim. Acta 46, 1480 (1963). Total synthesis of α- and β-forms: Komppa, Ann. Acad. Sci. Fenn. A59, 3 (1943), C.A. 41, 425 (1947); Thomas, Fallis, Tetrahedron Lett. 1973, 4687; eidem, J. Am. Chem. Soc. 98, 1227 (1976). Review: Palmer, Ind. Eng. Chem. 34, 1028 (1942); J. L. Simonsen, The Terpenes vol. II (Cambridge Univ. Press, 2nd ed., 1949) pp 105-191; D. V. Banthorpe, D. Whittaker, Chem. Rev. 66, 643-654 (1966); Food Cosmet. Toxicol. 16, Suppl. I, 853-857 (1978).

Chemical structure

Derivative

dl-Form.

Properties

Liquid, characteristic odor of turpentine. bp760 155-156°; bp20 52.5°. d420 0.8592. nD20 1.4664. Practically insol in water. Sol in alc, chloroform, ether, glacial acetic acid.

Derivative

Hydrochloride.
C10H17Cl; mol wt 172.69.
C 69.55%, H 9.92%, Cl 20.53%.

Properties

mp 132°.

Derivative

d-Form.

Properties

bp760 155-156°. d420 0.8591. nD20 1.4663. [α]D20 +51.14°.

Derivative

Hydrochloride.

Properties

mp 132°. [α]D20 +33.52° (alcohol).

Derivative

l-Form.

Properties

bp760 155-156°. d420 0.8590. nD20 1.4662. [α]D20 -51.28°.

Derivative

Hydrochloride.

Properties

mp 132°. [α]D20 -33.24° (alcohol).

Caution

Toxic effects similar to turpentine, q.v.

Use

Manufacture of camphor, insecticides, solvents, plasticizers, perfume bases, synthetic pine oil.