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Phenylacetaldehyde glyceryl acetal
Fragrance raw materials monographs PHENYLACETALDEHYDE
GLYCERYL
829 ACETAL
Synonyms: 5-Hydroxymethyl-2-benzyl-1,3-dioxolan; 5-hydroxy-2-benzyl-1,3dioxan; 2-benzyl-4-hydroxymethyl- 1,3-dioxolane. Structure: C6H5.CHZ.CH.0.CHZ.CH.CHzOH and C6H5.CH,.CH.0.Cfi,.CHOH.CH,. t A I L.---o-’ Description and physical properties: A colourless viscous liquid. Occurrence: Has apparently not been reported to occur in nature. Preparation: From phenylacetaldehyde and glycerol by condensation (Arctander, 1969). Uses: In public use since the 1930s. Use in fragrances in the USA amounts to approximately 6000 lb/yr. Concentration in final product (%): Soap 0.02 0.15
Usual Maximum Analytical
data: Gas chromatogram,
Detergent 0.002 0.015 RIFM
Creams, lotions 0.01 0.05
no. 72-6; infra-red curve, RIFM
Perfume 0.2 1.0 no. 72-6.
Phenylacetaldehyde glyceryl acetal was given GRAS status by FEMA (1965) and is approved by the FDA for food use (21 CFR 121.1164). The Council of Europe (1974) included phenylacetaldehyde glyceryl acetal at a level of 20ppm in the list of artificial flavouring substances that may be added to foodstuffs without hazard to public health. Biological
data
Acute toxicity. The acute oral LDso value in rats was reported as 1.72 ml/kg (1.57-1.87ml/kg) and the acute dermal LD,, value in rabbits exceeded Zg/kg (Moreno, 1972). The ip LD,, for mice was found to be 2.7, + 0.23 mmol/kg (523.8 f 44.62 mg/kg) and the mean paralysing dose (ED,,) for ip administration to mice was found to be 0.77 _+ 0.07 mmol/kg (Berger, 1951). Irritation. Phenylacetaldehyde glyceryl acetal applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was moderately irritating (Moreno, 1972). Tested at 3% in petrolatum it produced no irritation after a 48-hr closed-patch test on human subjects (Kligman, 1972). Sensitization. A maximization test (Kligman, 1966; Kligman & Epstein, 1975) was carried out on 25 volunteers. The material was tested at a concentration of 3% in petrolatum and produced no sensitization reactions (Kligman, 1972). Micro-organisms. Phenylacetaldehyde glyceryl acetal was found by a zone-inhibition technique to be an effective antibacterial agent against Gram-positive Staphylococcus aureus and six Gram-negative bacteria, including Pseudomonas aeruginosa (Felton & Kapp, 1970). Metabolism. Acetals hydrolyse readily in the presence of acids to generate the corresponding aldehydes and alcohols (Fassett, 1963).
References Arctander, S. (1969). Perjkme und Flavor Chemicals (Aroma Chemicals). Vol. 2, no. 2488. S. Arctander, Montclair, New Jersey. Berger, F. M. (1951). The paralysing activity of some substituted dioxolanes in relation to their structure. Archs
inc. Pharmacodyn.
Thbr.
85, 414.
Council of Europe (1974). Natural Flavouring Substances, Their Sources, and Added Artificial Flavouring Substances. Partial Agreement in the Sociai and Public Health Field. List 1, no. 41, p. 132. Strasbourg. Fassett, D. W. (1963). Aldehvdes and acetals. In Industrial Hvaiene and Toxicoloav. II 2nd Ed. Edited bv, F. A. Patty. Vol. Ii, p. 1984. In&science Publishers, New York. ‘” Felton, S. M. & Kapp, I. B. (1970). A new class of broad-spectrum antibacterials. TGA Cosmet. J. (Toilet Goods
Ass.) 2 (1). 16.
Flavoring Extract Manufacturers’ Association (1965). Survey of flavoring ingredient usage levels. No. 2877. Fd Technol., Champaign 19 (2), part 2, 155. Kligman, A. M. (1966). The identification of contact allergens by human assay. III. The maximization test. A procedure for screening and rating contact sensitizers. J. invest. Derm. 47. 393. Kligman, A. M. (1972). Report to RIFM, 1 June. Kligman, A. M. & Epstein, W. (1975). Updating the maximization test for identifying contact allergens. Contact Dermutitis 1, 231. Moreno, 0. M. (1972). Reports to RIFM, 19 February and 14 March.
GLYCERYL
829 ACETAL
Synonyms: 5-Hydroxymethyl-2-benzyl-1,3-dioxolan; 5-hydroxy-2-benzyl-1,3dioxan; 2-benzyl-4-hydroxymethyl- 1,3-dioxolane. Structure: C6H5.CHZ.CH.0.CHZ.CH.CHzOH and C6H5.CH,.CH.0.Cfi,.CHOH.CH,. t A I L.---o-’ Description and physical properties: A colourless viscous liquid. Occurrence: Has apparently not been reported to occur in nature. Preparation: From phenylacetaldehyde and glycerol by condensation (Arctander, 1969). Uses: In public use since the 1930s. Use in fragrances in the USA amounts to approximately 6000 lb/yr. Concentration in final product (%): Soap 0.02 0.15
Usual Maximum Analytical
data: Gas chromatogram,
Detergent 0.002 0.015 RIFM
Creams, lotions 0.01 0.05
no. 72-6; infra-red curve, RIFM
Perfume 0.2 1.0 no. 72-6.
Phenylacetaldehyde glyceryl acetal was given GRAS status by FEMA (1965) and is approved by the FDA for food use (21 CFR 121.1164). The Council of Europe (1974) included phenylacetaldehyde glyceryl acetal at a level of 20ppm in the list of artificial flavouring substances that may be added to foodstuffs without hazard to public health. Biological
data
Acute toxicity. The acute oral LDso value in rats was reported as 1.72 ml/kg (1.57-1.87ml/kg) and the acute dermal LD,, value in rabbits exceeded Zg/kg (Moreno, 1972). The ip LD,, for mice was found to be 2.7, + 0.23 mmol/kg (523.8 f 44.62 mg/kg) and the mean paralysing dose (ED,,) for ip administration to mice was found to be 0.77 _+ 0.07 mmol/kg (Berger, 1951). Irritation. Phenylacetaldehyde glyceryl acetal applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was moderately irritating (Moreno, 1972). Tested at 3% in petrolatum it produced no irritation after a 48-hr closed-patch test on human subjects (Kligman, 1972). Sensitization. A maximization test (Kligman, 1966; Kligman & Epstein, 1975) was carried out on 25 volunteers. The material was tested at a concentration of 3% in petrolatum and produced no sensitization reactions (Kligman, 1972). Micro-organisms. Phenylacetaldehyde glyceryl acetal was found by a zone-inhibition technique to be an effective antibacterial agent against Gram-positive Staphylococcus aureus and six Gram-negative bacteria, including Pseudomonas aeruginosa (Felton & Kapp, 1970). Metabolism. Acetals hydrolyse readily in the presence of acids to generate the corresponding aldehydes and alcohols (Fassett, 1963).
References Arctander, S. (1969). Perjkme und Flavor Chemicals (Aroma Chemicals). Vol. 2, no. 2488. S. Arctander, Montclair, New Jersey. Berger, F. M. (1951). The paralysing activity of some substituted dioxolanes in relation to their structure. Archs
inc. Pharmacodyn.
Thbr.
85, 414.
Council of Europe (1974). Natural Flavouring Substances, Their Sources, and Added Artificial Flavouring Substances. Partial Agreement in the Sociai and Public Health Field. List 1, no. 41, p. 132. Strasbourg. Fassett, D. W. (1963). Aldehvdes and acetals. In Industrial Hvaiene and Toxicoloav. II 2nd Ed. Edited bv, F. A. Patty. Vol. Ii, p. 1984. In&science Publishers, New York. ‘” Felton, S. M. & Kapp, I. B. (1970). A new class of broad-spectrum antibacterials. TGA Cosmet. J. (Toilet Goods
Ass.) 2 (1). 16.
Flavoring Extract Manufacturers’ Association (1965). Survey of flavoring ingredient usage levels. No. 2877. Fd Technol., Champaign 19 (2), part 2, 155. Kligman, A. M. (1966). The identification of contact allergens by human assay. III. The maximization test. A procedure for screening and rating contact sensitizers. J. invest. Derm. 47. 393. Kligman, A. M. (1972). Report to RIFM, 1 June. Kligman, A. M. & Epstein, W. (1975). Updating the maximization test for identifying contact allergens. Contact Dermutitis 1, 231. Moreno, 0. M. (1972). Reports to RIFM, 19 February and 14 March.