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Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

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RIFM fragrance ingredient safety assessment, 2-pentylcyclopentan-1-one, CAS Registry Number 4819-67-4.

Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association·2017
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RIFM fragrance ingredient safety assessment, menthyl acetate (isomer unspecified), CAS Registry Number 16409-45-3.

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Fragrance material review on 3-phenyl-1-propanol.

S P Bhatia1, G A Wellington, J Cocchiara

  • 1Research Institute for Fragrance Materials Inc., 50 Tice Boulevard, Woodcliff Lake, NJ 07677, USA. sbhatia@rifm.org

Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association
|August 23, 2011
PubMed
Summary

This review summarizes toxicology and dermatology data for 3-phenyl-1-propanol, a fragrance ingredient. The chemical shows little toxic potential, with available data supporting its safe use in fragrances.

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Area of Science:

  • Toxicology
  • Dermatology
  • Fragrance Chemistry

Background:

  • 3-Phenyl-1-propanol belongs to the cinnamyl phenylpropyl fragrance group.
  • This group features aryl-substituted primary alcohols/aldehydes/esters with low toxic potential.
  • These compounds share metabolic pathways with cinnamic acid derivatives.

Purpose of the Study:

  • To present a toxicologic and dermatologic review of 3-phenyl-1-propanol.
  • To summarize available data on this specific fragrance ingredient.
  • To inform a broader safety assessment of cinnamyl phenylpropyl compounds.

Main Methods:

  • Comprehensive literature review of toxicology and dermatology studies.
  • Evaluation and summarization of physical properties, acute toxicity, skin irritation, and sensitization data.
  • Assessment of in vitro skin absorption and mutagenicity.

Main Results:

  • Compiled data on physical properties, acute toxicity, skin irritation, and sensitization.
  • Included findings on in vitro skin absorption and mutagenicity.
  • Data supports the low toxic potential of 3-phenyl-1-propanol.

Conclusions:

  • 3-Phenyl-1-propanol exhibits low toxic potential.
  • The summarized data contributes to the overall safety assessment of cinnamyl phenylpropyl fragrance ingredients.
  • Refer to Belsito et al. (2011) for comprehensive safety assessment.