7167. Perillaldehyde

Nomenclature

CAS number: 2111-75-3
4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde; 4-isopropenyl-1-cyclohexene-1-carboxaldehyde.
C10H14O; mol wt 150.22.
C 79.95%, H 9.39%, O 10.65%.

Description and references

Isoln from Perilla arguta Benth., Labiatae: Semmler, Zaar, Ber. 44, 52, 815 (1911); from essential oil of Sium latifolium L., Umbelliferae: Parczewski, Diss. Pharm. 12, 223 (1960), C.A. 55, 7765c (1961); from mandarin peel oil (Citrus reticulata Blanco, Rutaceae): Kugler, Kováts, Helv. Chim. Acta 46, 1480 (1963). Prepn by chromic oxidation of perilla alcohol: Naves, ibid. 29, 553 (1946); Ritter, Ginsburg, J. Am. Chem. Soc. 72, 2381 (1950); Kergomard, Philibert-Bigou, Bull. Soc. Chim. Fr. 1958, 393, 1174; Naves, Grampoloff, ibid. 1960, 37. Brief review: Food Chem. Toxicol. 20, Suppl. I-IV, 799-800 (1982).

Chemical structure

Properties

LD50 in mice (g/kg): 1.72 orally; in guinea pigs (g/kg): >5 dermally (Food Chem. Toxicol.).

Derivative

d-Form.

Properties

Liquid. bp745 237°; bp7 98-100°. d420 0.953. nD20 1.5058. [α]D20 +127° (c = 13.1 in carbon tetrachloride).

Derivative

l-Form.

Properties

Liquid. bp10 104-105°. d420 0.9645. nD20 1.5069. [α]D20 -146°.

Derivative

Oxime.

Nomenclature

CAS number: 138-91-0
l-Perillaldehyde α-syn-oxime; perillartine; “perilla sugar”.
C10H15NO; mol wt 165.23.
C 72.69%, H 9.15%, N 8.48%, O 9.68%.

Description and references

Previously referred to as l-perillaldehyde α-anti-oxime. Synthesis: And^o et al., Science (Tokyo) 17, 241 (1947), C.A. 45, 1976d (1951). Clarification of structure: Acton et al., Experientia 26, 473 (1970).

Properties

Needles, mp 102°. uv max (alc): 232 nm (ε 21800). About 2000 times as sweet as sucrose: Furukawa, Koryo No. 11, 11, 40 (1950), C.A. 44, 6083g (1950).

Use

The oxime is used as sweetening agent in Japan.