Introduction
11
Editorial Introduction The Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol Simple Acid Ester Derivatives (AAASAE) comprise two economically important classes of chemically and metabolically related fra- grance ingredients. The AAA and AAASAE fragrance ingredients are structurally diverse and include primary, secondary, and ter- tiary alkyl alcohols that have as their aryl core either a substituted or unsubstituted benzene ring. The AAA and AAASAE fragrance ingredients merit independent safety assessments based on the quantity of their use and potential consumer exposures (Ford, 2000). However, it is also appropriate that the two safety assessments be presented together in one issue. Although comprehensive and independent toxicology databases exist for both the AAA and AAASAE fragrances, in many cases AAA- SAE compounds may be readily hydrolyzed in vivo by carboxyl esterases to generate an economically important AAA fragrance ingredient. Thus, on the basis of common metabolic pathways, the toxicology for an AAA fragrance ingredient should also be rel- evant for its corresponding AAASAE derivative. The large majority of the AAA and AAASAE fragrance ingredi- ents, that will be discussed in the following safety assessments, have common aryl alcohol cores and have been grouped accord- ingly based on structural similarities. Table 1 illustrates the AAA/ AAASAE derived from common primary Aryl Alkyl Alcohols; Table 2 indicates the AAA/AAASAE derived from common secondary Aryl Alkyl Alcohols and Table 3 includes the AAA/AAASAE derived from common tertiary aryl alcohols. The several AAASAE fragrances for which there are no comparable AAAs and AAA fragrances for which there are no comparable AAASAEs are also noted. Table 1 Comparison of primary Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). Primary AAA Structure AAASAE Structure Anisyl alcohol CAS# 105-13-5 p-Anisyl acetate CAS# 104-21-2 Anisyl butyrate CAS# 6963-56-0 (continued on next page) 0278-6915/$ - see front matter Ó 2012 Elsevier Ltd. All rights reserved. doi:10.1016/j.fct.2012.02.036 Food and Chemical Toxicology 50 (2012) S41–S51 Contents lists available at SciVerse ScienceDirect Food and Chemical Toxicology journal homepage: www.elsevier.com/locate/foodchemtox
Transcript of Introduction
Food and Chemical Toxicology 50 (2012) S41–S51
Contents lists available at SciVerse ScienceDirect
Food and Chemical Toxicology
journal homepage: www.elsevier .com/ locate/ foodchemtox
Editorial
Introduction
The Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol SimpleAcid Ester Derivatives (AAASAE) comprise two economicallyimportant classes of chemically and metabolically related fra-grance ingredients. The AAA and AAASAE fragrance ingredientsare structurally diverse and include primary, secondary, and ter-tiary alkyl alcohols that have as their aryl core either a substitutedor unsubstituted benzene ring.
The AAA and AAASAE fragrance ingredients merit independentsafety assessments based on the quantity of their use and potentialconsumer exposures (Ford, 2000). However, it is also appropriatethat the two safety assessments be presented together in one issue.
Although comprehensive and independent toxicology databasesexist for both the AAA and AAASAE fragrances, in many cases AAA-SAE compounds may be readily hydrolyzed in vivo by carboxyl
Table 1Comparison of primary Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol Simple Acid Este
Primary AAA Structure AA
Anisyl alcoholCAS# 105-13-5
p-ACAS
AniCAS
0278-6915/$ - see front matter � 2012 Elsevier Ltd. All rights reserved.doi:10.1016/j.fct.2012.02.036
esterases to generate an economically important AAA fragranceingredient. Thus, on the basis of common metabolic pathways,the toxicology for an AAA fragrance ingredient should also be rel-evant for its corresponding AAASAE derivative.
The large majority of the AAA and AAASAE fragrance ingredi-ents, that will be discussed in the following safety assessments,have common aryl alcohol cores and have been grouped accord-ingly based on structural similarities. Table 1 illustrates the AAA/AAASAE derived from common primary Aryl Alkyl Alcohols; Table2 indicates the AAA/AAASAE derived from common secondary ArylAlkyl Alcohols and Table 3 includes the AAA/AAASAE derived fromcommon tertiary aryl alcohols. The several AAASAE fragrances forwhich there are no comparable AAAs and AAA fragrances for whichthere are no comparable AAASAEs are also noted.
rs (AAASAE).
ASAE Structure
nisyl acetate# 104-21-2
syl butyrate# 6963-56-0
(continued on next page)
Table 1 (continued)
Primary AAA Structure AAASAE Structure
Anisyl formateCAS# 122-91-8
Anisyl propionateCAS# 7549-33-9
(4-Methoxyphenyl)methyl isobutyrateCAS# 71172-26-4
Piperonyl acetateCAS# 326-61-4
2-MethoxybenzylalcoholCAS# 612-16-8
No correspondingAAASAE
Anisyl alcohol (mixo,m.p butpredominately p)CAS# 1331-81-3
No correspondingAAASAE
(continued on next page)
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
Benzyl alcoholCAS# 100-51-6
Benzyl acetateCAS# 140-11-4
Benzyl acetoacetateCAS# 5396-89-4
Benzyl butyrateCAS# 103-37-7
Benzyl formateCAS# 104-57-4
Benzyl isobutyrateCAS# 103-28-6
(continued on next page)
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
Benzyl propionateCAS# 122-63-4
Carbonic acid, methylphenylmethyl esterCAS# 13326-10-8
p-Tolyl alcoholCAS# 589-18-4
4-MethylbenzylacetateCAS# 2216-45-7
2,4-DimethylbenzylacetateCAS# 62346-96-7
p-IsopropylbenzylalcoholCAS# 536-60-7
p-IsopropylbenzylacetateCAS# 59230-57-8
b-MethylphenethylalcoholCAS# 1123-85-9
2-Phenylpropyl acetateCAS# 10402-52-5
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
2-(4-Methylphenoxy)-ethanolCAS# 15149-10-7
2-(p-Tolyloxy)ethylacetateCAS# 6807-11-0
Phenethyl alcoholCAS# 60-12-8
Phenethyl acetateCAS# 103-45-7
Phenethyl butyrateCAS# 103-52-6
Phenethyl formateCAS# 104-62-1
Phenethyl isobutyrateCAS# 103-48-0
p-TolylethanolCAS# 699-02-5
o-TolylethanolCAS# 19819-98-8
Phenethyl propionateCAS# 122-70-3
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
2-(4-tert. Butyl phenyl)ethanolCAS# 5406-86-0
2-(3-Methylphenyl)ethanolCAS# 1875-89-4
Benzeneethanol, b-methoxy-CAS# 2979-22-8
2-Hydroxy-2-phenylethyl acetateCAS# 10522-41-5
2-PhenoxyethanolCAS# 122-99-6
2-PhenoxyethylisobutyrateCAS# 103-60-6
2-PhenoxyethylpropionateCAS# 23495-12-7
PhenylpropanolCAS# 1335-12-2
3-Phenylpropyl acetateCAS# 122-72-5
2,2-Dimethyl-3-phenylpropanolCAS# 13351-61-6
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
Benzenepropanol,b,b,3-trimethylCAS# 103694-68-4
3-(p-Isopropyl)phenyl-2-methyl-1-propanolCAS# 4756-19-8
3-Methyl-5-phenylpentanolCAS# 55066-48-3
2-BenzylheptanolCAS# 92368-90-6
2-Methyl-4-phenylpentanolCAS# 92585-24-5
No correspondingAAASAE
2-Methyl-5-phenylpentanolCAS# 25634-93-9
No correspondingAAASAE
5-PhenylpentanolCAS# 10521-91-2
3-Phenyl-2-butenylacetateCAS# 20883-16-3
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Table 1 (continued)
Primary AAA Structure AAASAE Structure
3-Phenyl-3-buten-1-ylacetateCAS# 7306-12-9
Table 2Comparison of Secondary Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol Simple Acid Esters (AAASAE).
Secondary AAA Structure AAASAE Structure
a-Methylbenzyl alcoholCAS# 98-85-1
a-Methylbenzyl acetateCAS# 93-92-5
a-Methylbenzyl propionateCAS# 120-45-6
a-Isobutylphenethyl alcoholCAS# 7779-78-4
2-Acetoxy-1-phenylpropaneCAS# 2114-33-2
1,3-Dimethyl-3-phenylbutyl acetateCAS# 68083-58-9
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Table 2 (continued)
Secondary AAA Structure AAASAE Structure
3-Methyl-1-phenylbutan-2-olCAS# 705-58-8
a-Propylphenethyl alcoholCAS# 705-73-7
Table 3Comparison of Tertiary Aryl Alkyl Alcohols (AAA) and Aryl Alkyl Alcohol Simple Acid Esters (AAASAE).
Tertiary AAA Structure AAASAE Structure
a,a-Dimethylphenethyl alcoholCAS# 100-86-7
1,1-Dimethyl-2-phenylethyl isobutyrateCAS# 59354-71-1
1,1-Dimethyl-2-phenylethyl acetateCAS# 151-05-3
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Table 3 (continued)
Tertiary AAA Structure AAASAE Structure
1,1-Dimethyl-2-phenylethyl butyrateCAS# 10094-34-5
1,1-Dimethyl-2-phenylethyl formateCAS# 10058-43-2
1,1-Dimethyl-2-phenylethyl propionateCAS# 67785-77-7
2-Phenyl-2-propanolCAS# 617-94-7
p-a,a-Trimethylbenzyl alcoholCAS# 1197-01-9
a,a,4-Trimethylphenethyl alcoholCAS# 20834-59-7
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Table 3 (continued)
Tertiary AAA Structure AAASAE Structure
2-Methyl-4-phenyl-2-butanolCAS# 103-05-9
2-Methyl-4-phenyl-2-butyl isobutyrateCAS# 10031-71-7
2-Methyl-4-phenyl-2-butyl acetateCAS# 103-07-1
1-Phenyl-3-methyl-3-pentanolCAS# 10415-87-9
1-Phenyl-3-methyl-3-pentyl acetateCAS# 72007-81-9
BenzhydrolCAS# 91-01-0
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