Cetyl alcohol

Identification

Name
Cetyl alcohol
Accession Number
DB09494
Type
Small Molecule
Groups
Approved
Description

Cetyl alcohol, also known as 1-hexadecanol or n-hexadecyl alcohol, is a 16-C fatty alcohol with the chemical formula CH3(CH2)15OH. It can be produced from the reduction of palmitic acid. Cetyl alcohol is present in a waxy white powder or flake form at room temperature, and is insoluble in water and soluble in alcohols and oils [1]. Discovered by Chevrenl in 1913, cetyl alcohol is one of the oldest known long-chain alcohol [1]. It may be contained in cosmetic and personal care products such as shampoos, creams and lotions. Mainly it is used as an opacifier, emulsifier, and thickening agent that alter the thickness of the liquid, and increase and stabilize the foaming capacity. Due to its water-binding property, cetyl alcohol is commonly used as an emollient that prevents drying and chapping of the skin [1]. According to the FDA Code of Federal Regulations, cetyl alcohol is a safe synthetic fatty acid in food and in the synthesis of food components under the condition that it contain not less than 98 percent of total alcohols and not less than 94 percent of straight chain alcohols [3]. Cetyl alcohol is also listed in the OTC ingredient list as a skin protectant for skin irritations caused by poison ivy, oak, sumac, and insect bites or stings [4]. Cetyl alcohol is reported to be a mild skin or eye irritant.

Structure
Thumb
Synonyms
  • hexadecan-1-ol
  • palmityl alcohol
External IDs
FEMA NO. 2554 / NSC-4194
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
All Day Skin Relief with Colloidal OatsLotion80 mg/100mLTopicalShanghai Lantern Cosmetic Co2016-05-16Not applicableUs
All Day Skin Relief with Colloidal OatsLotion80 mg/100mLTopicalNingbo Liyuan2016-05-132016-05-16Us
All Day Skin Relief with Colloidal OatsLotion80 mg/100mLTopicalLantern Enterprises Ltd.2016-05-13Not applicableUs
Daily Moisturizing with Colloidal OatsLotion80 mg/100mLTopicalLantern Enterprises Ltd.2016-05-13Not applicableUs
Daily Moisturizing with Colloidal OatsLotion80 mg/100mLTopicalNingbo Liyuan2016-05-132016-05-16Us
Daily Moisturizing with Colloidal OatsLotion80 mg/100mLTopicalShanghai Lantern Cosmetic Co2016-05-16Not applicableUs
Categories
UNII
936JST6JCN
CAS number
36653-82-4
Weight
Average: 242.4406
Monoisotopic: 242.26096571
Chemical Formula
C16H34O
InChI Key
BXWNKGSJHAJOGX-UHFFFAOYSA-N
InChI
InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
IUPAC Name
hexadecan-1-ol
SMILES
CCCCCCCCCCCCCCCCO

Pharmacology

Indication

No therapeutic indications in medicinal products. Indicated to be used as an indirect additive in food contact substances, or an ingredient in commercial or cosmetic products.

Associated Conditions
Pharmacodynamics

Cetyl alcohol exhibits skin protect properties against skin irritations caused by bites, rashes and stings. The inhibitory action of cetyl alcohol against the growth of Mycoplasma gallisepticum and Mycopiasma pneumoniae has been reported [1].

Mechanism of action

Cetyl alcohol has hydrating properties that makes it a suitable emulsifier and stabilizer in pharmaceutical formulations. It is also present in washable ointment base due to its dispersant abilities and stabilizing properties [1]. Potential antimicrobial activity of cetyl alcohol may be due to a change in cell membrane permeability that either blocks absorption of essential nutrients and induction of outward diffusion vital cellular components [1]. This proposed mechanism of action is thought to be similar for other long-chain aliphatic alcohols with same antimicrobial activity, such as myristyl alcohol and behenyl alcohol [1].

Absorption

Following ingestion at a dose level of 2.0 g/kg in rats, cetyl alcohol was partly absorbed [2]. Administration of 0.2 mg cetyl alcohol in rat by stomach tube indicated good absorption as 63-96 % of radiolabeled cetyl alcohol was detected in the lymph [1]. About 15% of total cetyl alcohol was unchanged during its passage through the mucosal cells of the small intestine but mostly underwent oxidation to palmitic acid [1]. The extent of absorption was reported to be 26% in poultry [1].

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Following ingestion at a dose level of 2.0 g/kg in rats, cetyl alcohol was partly metabolized to palmitic acid [2]. After administration of 0.2 mg cetyl alcohol in rat by stomach tube, cetyl alcohol was mostly oxidized to palmitic acid and incorporated into triglycerides and phospholipids during its passage through the mucosal cells of the small intestine [1].

Route of elimination

Following ingestion at a dose level of 2.0 g/kg in rats, about 20% of the dose was recovered as unchanged molecule in the feces [2]. This may be due to the interconvertibility of fatty acids and alcohols, resulting in the conversion of palmitic acid to cetyl alcohol during its passage through the intestinal mucosal cells into the intestinal lumen [1]. In rats, cetyl Alcohol was also excreted in the urine as conjugated glucuronic acid and as expired carbon dioxide [1].

Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral LD50 in mouse is 3200 mg/kg and acute dermal LD50 is >2600 mg/kg in rabbit [MSDS]. It is considered to be slightly toxic in humans in case of oral ingestion at doses of 5 g/kg and greater [1]. In a rat study, the effects of toxicity were mainly in the central nervous system (CNS) leading to CNS depression and difficulty in respiration after 7-14 days post-administration via stomach tube [1]. In a subchronic dermal toxicity study of rabbits, topical application of 11.5 % cetyl alcohol was associated with histological findings of keratosis, hyperkeratosis, and papillary projections of the epidermis, all of which are features of exfoliative dermatitis [1]. However it is concluded that there is no evidence of major skin irritation and systemic toxicity of cetyl alcohol. Inhalation of 26 ppm cetyl alcohol vapors in animals caused slight irritation of the mucous membranes of the eyes, nose, throat, and respiratory passages [1]. Cetyl Alcohol was not mutagenic in Salmonella typhimurium LT2 mutant strains in the spot test [1].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Elder RL et al.: Final Report on the Safety Assessment of Cetearyl Alcohol, Cetyl Alcohol, lsostearyl Alcohol, Myristyl Alcohol, and Behenyl Alcohol Journal of the American College of Toxicology. 1988 May 1;7(3):359-413.
  2. 1-HEXADECANOL - National Library of Medicine HSDB Database - Toxnet [Link]
  3. Synthetic Fatty Alcohols - FDA [Link]
  4. FDA OTC ingredients [Link]
External Links
Human Metabolome Database
HMDB0003424
PubChem Compound
2682
PubChem Substance
347827863
ChemSpider
2581
ChEBI
16125
ChEMBL
CHEMBL706
HET
PL3
Wikipedia
Cetyl_alcohol
PDB Entries
2uuu / 2uuv / 4quw / 4rc5 / 4rc7
MSDS
Download (47.5 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LotionTopical80 mg/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)49.3MSDS
boiling point (°C)344MSDS
water solubilityInsolubleNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000181 mg/mLALOGPS
logP7.17ALOGPS
logP6.14ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.35 m3·mol-1ChemAxon
Polarizability34.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f72-7931000000-00a8faa3fd4f0c38a405
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0f6t-9531000000-0dc2948d10d835886750
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9000000000-1be6f87af09f0bc4339f
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83
GC-MS Spectrum - EI-BGC-MSsplash10-0a59-9100000000-51d2315e018d6ebbe25d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f72-7931000000-00a8faa3fd4f0c38a405
GC-MS Spectrum - GC-MSGC-MSsplash10-0f6t-9531000000-0dc2948d10d835886750
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f72-9821000000-ee82a405e4a854526b64
Mass Spectrum (Electron Ionization)MSsplash10-0a5c-9000000000-f3299e52ea0593788e37
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0udi-0910000000-b74545433556690d2c46
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0udi-0900000000-7aab213ad736e774476c
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0udi-0900000000-55a8272e13510c85c06a
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0a4l-9000000000-a4776db6cf6d30dfb50e
MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , PositiveLC-MS/MSsplash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83
MS/MS Spectrum - EI-B (JEOL JMS-HX-100) , PositiveLC-MS/MSsplash10-0a59-9100000000-7ca85869bfef10e335f3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty alcohols
Direct Parent
Long-chain fatty alcohols
Alternative Parents
Primary alcohols / Hydrocarbon derivatives
Substituents
Long chain fatty alcohol / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain primary fatty alcohol, fatty alcohol 16:0 (CHEBI:16125) / Fatty alcohols (C00823) / Fatty alcohols (LMFA05000061) / a small molecule (CPD-348)

Drug created on November 30, 2015 12:10 / Updated on November 02, 2018 07:03