Perillaldehyde
Title: Perillaldehyde
CAS Registry Number: 2111-75-3
CAS Name: 4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde
Additional Names: 4-isopropenyl-1-cyclohexene-1-carboxaldehyde
Molecular Formula: C10H14O
Molecular Weight: 150.22
Percent Composition: C 79.95%, H 9.39%, O 10.65%
Literature 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).
Properties: LD50 in mice (g/kg): 1.72 orally; in guinea pigs (g/kg): >5 dermally (Food Chem. Toxicol.).
Toxicity data: LD50 in mice (g/kg): 1.72 orally; in guinea pigs (g/kg): >5 dermally (Food Chem. Toxicol.)
 
Derivative Type: d-Form
Properties: Liquid. bp745 237°; bp7 98-100°. d420 0.953. nD20 1.5058. [a]D20 +127° (c = 13.1 in carbon tetrachloride).
Boiling point: bp745 237°; bp7 98-100°
Optical Rotation: [a]D20 +127° (c = 13.1 in carbon tetrachloride)
Index of refraction: nD20 1.5058
Density: d420 0.953
 
Derivative Type: l-Form
Properties: Liquid. bp10 104-105°. d420 0.9645. nD20 1.5069. [a]D20 -146°.
Boiling point: bp10 104-105°
Optical Rotation: [a]D20 -146°
Index of refraction: nD20 1.5069
Density: d420 0.9645
 
Derivative Type: Oxime
CAS Registry Number: 138-91-0
Additional Names: l-Perillaldehyde a-syn-oxime; perillartine; "perilla sugar"
Molecular Formula: C10H15NO
Molecular Weight: 165.23
Percent Composition: C 72.69%, H 9.15%, N 8.48%, O 9.68%
Literature References: Previously referred to as l-perillaldehyde a-anti-oxime. Synthesis: Andô 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 (e 21800). About 2000 times as sweet as sucrose: Furukawa, Koryo No. 11, 11, 40 (1950), C.A. 44, 6083g (1950).
Melting point: mp 102°
Absorption maximum: uv max (alc): 232 nm (e 21800)
 
Use: The oxime is used as sweetening agent in Japan.

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