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1-Tetracosanol

HCID 10472
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Basic information

CAS
506-51-4
Standard SMILES
CCCCCCCCCCCCCCCCCCCCCCCCO
InChIKey
TYWMIZZBOVGFOV-UHFFFAOYSA-N
Molecular formula
C24H50O
Average molar mass
354.7 g/mol
Monoisotopic mass
354.38616621

Overview

Tetracosan-1-ol is a very long-chain primary fatty alcohol that is tetracosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group. It has been isolated from a variety of plants, including grape seeds, evening primrose (Oenothera biennis), pitaya fruits (Hylocereus polyrhizus and Hylocereus undatus), and the flowers of Arabian jasmine ( Jasminum sambac). It has a role as a vulnerary and a plant metabolite. It is a very long-chain primary fatty alcohol and a tetracosanol.

Names & identifiers

Preferred name
1-Tetracosanol
IUPAC
tetracosan-1-ol
English name
1-Tetracosanol
Molecular formula
C24H50O
Molecular weight
354.65

Names & synonyms

1-Tetracosanol506-51-4LIGNOCERYL ALCOHOLTetracosan-1-olLignoceroln-TetracosanolTetracosyl alcoholLignoceric alcoholn-Tetracosanol-12N0PI37IOCNSC 93768HSDB 5674
Show more names
TETRACOSANOLcarnaubyl alcoholALCOHOL C24etracosan-1-ol
UNII-2N0PI37IOCEINECS 208-043-9NSC-93768DTXSID8027161CHEBI:77413EC 208-043-9RefChem:25873DTXCID107161

Database identifiers

CAS
506-51-4
PubChem CID
10472
DTXSID
DTXSID8027161
ChEBI
CHEBI:77413
UNII
2N0PI37IOC
EC Number
208-043-9
Nikkaji
J116.891F

Properties

Computed structural properties

XLogP
11.6
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
22
Heavy atoms
25
Formal charge
0
Complexity
214

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
PolymersOther Classes -> Alcohols and Polyols, Other
DensityWaxy consistency ... lower specific density than water ... odorless except for traces of impurities such as carbonyl compounds and hydrocarbons, which are usually present. ... /Tetradecanol and higher alcohols/
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point210 °C at 0.4 mm Hg
Melting Point77 °C
Physical DescriptionWhite powder; [MSDSonline]
Other Experimental Properties · 2 items

Immiscible in water /Decanol and higher fatty alcohols/

Common organic solvents such as petroleum ether, lower alcohols, and diethyl ether are suitable solvents for fatty alcohols. /Fatty alcohols/

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 85.9% (128 of 149) of all reports.

Warning

H319 (10.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 149 reports by companies from 8 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: 1-Tetracosanol

REACH registered substance: Tetracosanol (EC: 208-043-9)

1-Tetracosanol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - 1-Tetracosanol: Human health tier I assessment
Hazards SummaryMay cause irritation; [MSDSonline]
Hazard Classes and CategoriesEye Irrit. 2 (10.1%)

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as intermediates; Fatty alcohols with chain lengths >18 are used to prevent evaporation of water reservoirs during dry seasons; Naturally occurring in lanolin and green leaf composite samples; [HSDB]

The industrial importance of fatty alcohols is due to the large number of reactions that the hydroxyl group may undergo ... many of the resulting derivatives are intermediates of commercial importance /Fatty alcohols/

Fatty alcohols with chain lengths greater than 18 ... are suitable for protection of water reservoirs against evaporation during dry seasons ... evaporation can be reduced up to 50% /Fatty alcohols/

U.S. Production · 1 item

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

General Manufacturing Information · 2 items

1-Tetracosanol: ACTIVE

Lanolin was saponified and extracted with petroleum ether. The natural fraction of lanolin obtained (wool wax alcohols) was treated with digitonin. After thin-layer chromatography, 5 fractions were isolated from the digitonin-negative fraction from which several steroidal hydrocarbons, including lignoceryl alcohol, were isolated.

Applications

Uses1-Tetracosanol is a useful reagent for organic synthesis.

Additional notes · 1 item

DefinitionChEBI: A long-chain primary fatty alcohol that is tetracosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group. It has been isolated from a variety of plants, including grape seeds, evening primrose (Oenothera bienn s), pitaya fruits (Hylocereus polyrhizus and Hylocereus undatus), and the flowers of Arabian jasmine ( Jasminum sambac).

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Related reactions

1 records
New reaction record
HRID 2242761 reaction equation
HRID 2242761As reactantuspto-grants-2010_03

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Physicochemical properties

Melting point
75 · 75-77 °C
Boiling point
190 °C · 190 °C
Density
0.839 · 0.839
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.4471 · 1.4471 (estimate)
Flash point
142 ℃ · 142℃
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Hexanes (Slightly)
pka
15.2 · 15.20±0.10(Predicted)
form
Shiny Flakes or Fluffy Powder
color
White
Viscosity
10.4 mm2/s · 10.4mm2/s
Water Solubility
1 μg/L · 1μg/L at 25℃
BRN
1777129 · 1777129
Henry's Law Constant
3.4 · 3.4×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C24H50O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25/h25H,2-24H2,1H3
InChIKey
TYWMIZZBOVGFOV-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCO
LogP
15 at · 15 at 20℃
CAS DataBase Reference
506 · 506-51-4(CAS DataBase Reference)
FDA UNII
2 N0PI37IOC · 2N0PI37IOC
EPA Substance Registry System
1 · 1-Tetracosanol (506-51-4)
UNSPSC Code
12352211 · 12352211
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
22 · 22-24/25
WGK Germany
-
TSCA
TSCA listed
HS Code
29051900 · 29051900
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
506 · 506-51-4(Hazardous Substances Data)
REACH Registrations
Active

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.1X10+5(SRC), determined from a structure estimation method(2), indicates that 1-tetracosanol is expected to be immobile in soil(SRC). Volatilization of 1-tetracosanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to mosit soil is expected to attenuate volatilization(SRC). 1-Tetracosanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006), but long chain linear alcohols are expected to biodegrade(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.1X10+5(SRC), determined from a structure estimation method(2), indicates that 1-tetracosanol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hours and 7.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 14 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 11(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006), but long chain linear alcohols are expected to biodegrade(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-tetracosanol, which has an estimated vapor pressure of 2.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase lignoceryl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-tetracosanol may be removed from the air by wet or dry deposition(SRC).

Plant Concentrations1-Tetracosanol emission rates from green leaf composite samples and dead leaves were 470 ug/g and 240 ug/g, respectively(1).
Effluent Concentrations · 1 item

1-Tetracosanol emission rates from wood smoke were calculated as 2.9 ug/g, 0.7 ug/g, and 2.9 ug/g from oak, eucalyptus and pine, respectively(1). 1-Tetracosanol emission rate from road dust samples was 22 ug/g(2). 1-Tetracosanol emission rate from pine wood (Pinus elliottii) smoke was measured at 1163 ng/g of burnt wood(3). 1-Tetracosanol was identified in smoke from the burning of chitin biopolymers(4).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-tetracosanol can be estimated to be 5.1X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-tetracosanol is expected to be immobile in soil.

Natural Pollution Sources1-Tetracosanol has been found in lanolin(1). 1-Tetracosanol emission rates from green leaf composite samples and dead leaves were 470 ug/g and 240 ug/g, respectively(2).
Artificial Pollution Sources · 1 item

1-Tetracosanol's production and possible use as a chemical intermediate(1) may result in its release to the environment through various waste streams. It's possible use as a water reservoir evaporation inhibitor(1) would result in its direct release to the environment.

Environmental BiodegradationBiodegradation data for lignoceryl alcohol were not available(SRC, 2006), but long chain linear alcohols are expected to biodegrade(1).
Sediment/Soil ConcentrationsSEDIMENT: 1-Tetracosanol was reported as extractable concentrations of 148 and 254 ng/g and bonded concentrations of 78 and 104 ng/g in anoxic continental slope sediment off southwestern Taiwan(1).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for 1-tetracosanol(SRC), using an estimated log Kow of 10.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 1-tetracosanol is estimated as 2.9X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-tetracosanol is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 7.6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 14 years if adsorption is considered(3). 1-Tetracosanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Tetracosanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-9 mm Hg(SRC), determined from a fragment constant method(4).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 1-tetracosanol with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Tetracosanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1281 workers (1064 of these are female) are potentially exposed to 1-tetracosanol in the US(1). Occupational exposure to 1-tetracosanol may occur through dermal contact with products containing this compound(SRC). Monitoring data indicate that the general population may be exposed to 1-tetracosanol via inhalation of ambient air and through dermal contact with products containing 1-tetracosanol(SRC).

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
-
tsca
TSCA listed
hs_code
29051900
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazardous Substances Data
506-51-4(Hazardous Substances Data)