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Lauryl sulfate

HCID 8778
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
151-41-7
Standard SMILES
CCCCCCCCCCCCOS(=O)(=O)O
InChIKey
MOTZDAYCYVMXPC-UHFFFAOYSA-N
Molecular formula
C12H26O4S
Average molar mass
266.4 g/mol
Monoisotopic mass
266.15518048

Overview

Dodecyl hydrogen sulfate is an alkyl sulfate. It is a conjugate acid of a dodecyl sulfate.

Names & identifiers

Preferred name
Lauryl sulfate
IUPAC
dodecyl hydrogen sulfate
English name
dodecyl hydrogen sulphate
Molecular formula
C12H26O4S
Molecular weight
266.4

Names & synonyms

Lauryl sulfateDODECYL SULFATE151-41-7Dodecyl hydrogen sulphateLauryl sulphateSulfuric acid, monododecyl esterN-Dodecyl sulfateMonododecyl hydrogen sulfateDodecylsulfuric acidDodecansulfonic acid, hydroxy-DIQ16UC154DTXSID0042088
Show more names
Brn 1710530LAURYLSULPHATEDODECYLSULPHATEN-DODECYLSULPHATE1-Dodecanol sulfateodecylhydrogensulfateSulfuric acid dodecyl esterhydroxy-dodecansulfonic aci
CHEBI:23872laurylsulfateRefChem:58313DTXCID8022088205-791-8Dodecyl hydrogen sulfateLauryl sulfuric acid(Dodecyloxy)sulfonic acid

Database identifiers

CAS
151-41-7
PubChem CID
8778
DTXSID
DTXSID0042088
ChEMBL
CHEMBL1204779
ChEBI

Properties

Computed structural properties

XLogP
4.7
Topological polar surface area
72 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
12
Heavy atoms
17
Formal charge
0
Complexity
244

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Emulsifiers/Surfactants
DrugsPharmaceuticals -> Listed in ZINC15
SurfactantsSurfactant -> linear alkylbenzyl sulfonate (LAS)
DecompositionWhen heated to decomposition it emits toxic fumes of (sulfur oxide).
Melting Point25-27 °C
Collision Cross Section166.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID4027076]
Other Experimental PropertiesPROTEIN BINDING ENERGY: -11 KCAL/MOLE

Physicochemical properties

Melting point
25 · 25-27 °C
Boiling point
379.6 °C · 379.6°C (rough estimate)

Safety & regulation

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

Hazard information

Regulatory Information · 2 items

Chemical: Sulfuric acid, monododecyl ester

Sulfuric acid, monododecyl ester: 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.

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Protective Action Criteria (PAC) · 3 items

3.9 [mg/m3]

43 [mg/m3]

260 [mg/m3]

Toxicology

InteractionsSURFACTANTS WERE INCORPORATED INTO MIXT WITH AMMONIUM THIOGLYCOLATE & APPLIED TO CLIPPED SKIN OF RABBITS DAILY FOR 20 DAYS. DAILY DOSAGE CAUSING 50% MORTALITY WAS DETERMINED. HIGHEST ACTIVITY WAS FOUND WITH TECHNICAL LAURYL SULFATE.
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+4(SRC), determined from a structure estimation method(2), indicates that dodecyl sulfate is expected to be immobile in soil(SRC). Volatilization of dodecyl sulfate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dodecyl sulfate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-8 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation of dodecyl sulfate in soil may be an important fate process since it is fairly biodegradable in aqueous biodegradation tests(5).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

METAB OF LAURYL SULFATE IN MAN & RAT WAS VIRTUALLY COMPLETE &...INDEPENDENT OF NATURE OF SALT FORM. COMPD WAS METABOLIZED BY OMEGA-HYDROXYLATION & WAS EVENTUALLY CONVERTED INTO BUTYRIC ACID 4-SULFATE. ... IN MAN A SECOND ROUTE...INVOLVED CLEAVAGE OF SULFATE LINKAGE & OXIDN OF RESULTING ALC /9-16% OF DOSE/.

BUTYRIC ACID 4-SULFATE PROBABLY ARISES BY OMEGA-OXIDATION OF DODECYL SULFATE TO A FATTY ACID-LIKE COMPD, WHICH IS THEN DEGRADED BY BETA-OXIDATION.

BUTYRIC ACID 4-SULFATE, PRODUCT OF DODECYL SULFATE METAB, WAS PARTIALLY DEGRADED NONENZYMICALLY IN RATS TO INORG SULFATE IONS & GAMMA-BUTYROLACTONE. THE LATTER COMPD MAY BE CONVERTED TO GAMMA-HYDROXYBUTYRATE BY ENZYME LACTONASE.

MeSH Pharmacological Classification · 1 item

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics.

Absorption, Distribution and ExcretionEIGHTY-EIGHT PERCENT OF RADIOLABEL FROM (14)C-LABELED PROPIONYL ERYTHROMYCIN LAURYL SULFATE EXCRETED IN URINE IN 24 HR FOLLOWING SINGLE ORAL DOSE. MORE THAN 95% WAS BUTYRIC ACID 4-SULFATE, A DERIVATIVE OF LAURYL SULFATE MOIETY.

Uses & manufacturing

Uses · 5 items

Used in shampoos, waste water treatment, and to make its salts (used as surfactants); [HSDB]

Sewer and Wastewater Treatment [Category: Industry]

USED IN SHAMPOOS

IN TREATMENT OF WASTE WATER

CHEM INT FOR SALTS, INCL SODIUM & AMMONIUM, USED AS SURFACTANTS

U.S. Production(1984) 4.2X10+10 g (INCL. SALTS)
Consumption PatternsESSENTIALLY 100% AS A CHEM INT FOR SALTS USED AS SURFACTANTS (1976)

Related reactions

4 records
New reaction record
HRID 359556 reaction equation
HRID 359556As productuspto-grants-1991_03
HRID 373212 reaction equation
HRID 373212As productuspto-grants-1992_11
HRID 1032381 reaction equation
HRID 1032381As productuspto-grants-1990_09
HRID 1589239 reaction equation
HRID 1589239As productuspto-grants-1986_02

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEBI:45599
UNII
DIQ16UC154
EC Number
205-791-8
Nikkaji
J90.686G
Density
1.1558 · 1.1558 (rough estimate)
refractive index
1.522 · 1.5220 (estimate)
pka
-3.29 · -3.29±0.18(Predicted)
Henry's Law Constant
5.5 · 5.5×101 mol/(m3Pa) at 25℃, HSDB (2015)
FDA UNII
16 UC154 · DIQ16UC154
EPA Substance Registry System
Lauryl sulfate (151-41-7)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
280 · P280-P305+P351+P338
TSCA
TSCA listed
Hazardous Substances Data
151 · 151-41-7(Hazardous Substances Data)

AQUATIC FATE: Based on a classification scheme(1) and an estimated Koc value of 1.0X10+4(SRC), determined from an estimation method(2), dodecyl sulfate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 71(SRC), from an estimated log Kow of 2.4(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate. Biodegradation of dodecyl sulfate in water may be an important fate process since it is fairly biodegradable in aqueous biodegradation tests(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dodecyl sulfate, which has an estimated vapor pressure of 3.2X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dodecyl sulfate may be removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dodecyl sulfate can be estimated to be 1.0X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that dodecyl sulfate is expected to be immobile in soil.

Human Toxicity Excerpts · 3 items

SHAMPOOS CONTAINING DODECYL SULFATE DID NOT IRRITATE SKIN OF HEALTHY ADULTS OR OF ELDERLY PERSONS WITH VARIETY OF COMMON DISORDERS.

SKIN IS SENSITIZED BY SYNTHETIC DETERGENTS CONTAINING, IN MOST CASES 22% OF ACTIVE COMPONENT AS LAURYL SULFATE, SULFONOL, CATION-ACTIVE AND NON-IONOGENIC PREPN.

Moderately toxic by ingestion.

Artificial Pollution SourcesDodecyl sulfate's production and use as a surfactant(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 3 items

SURFACTANTS ARE TREATED WITH PSEUDOMONAS TO DECOMPOSE THEM IN WASTEWATER. LF 2102 BACTERIA CULTURE WAS TREATED WITH SOLN CONTAINING 1000 PPM DODECYL ALCOHOL SULFATE. DECOMP WAS 100%.

DISSOLVED ORGANIC CARBON ELIMINATION RATE FROM ACTIVATED SLUDGE WAS 80-100% FOR LAURYL SULFATE.

AEROBIC: Dodecyl sulfate, present at approximately 50 mg/l, reached 70% of its theoretical BOD (93% DOC removal) in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). Initially present at approximately 10 mg/l, 69% DOC removal was measured after 28 days (preceded by a 14 day acclimation period) using the Sturm method(2).

Environmental Bioconcentration · 1 item

An estimated BCF of 71 was calculated for dodecyl sulfate(SRC), using an estimated log Kow of 2.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

Volatilization from Water/Soil · 1 item

The Henry's Law constant for dodecyl sulfate is estimated as 1.8X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dodecyl sulfate is expected to be essentially nonvolatile from water surfaces(2). Dodecyl sulfate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity ExcerptsHISTOLOGICAL AND MORPHOLOGICAL CHANGES IN ALL STRUCTURES OF NEPHRON & RENAL VASCULAR SYSTEM OF DOGS FED SMALL DAILY DOSES OF LAURYL SULFATE-BASED DETERGENT (0.5 MG LAURYL SULFATE/KG/DAY) FOR 110 DAYS.
Probable Routes of Human Exposure · 1 item

Occupational exposure to dodecyl sulfate may occur through inhalation and dermal contact with this compound at workplaces where dodecyl sulfate is produced or used. The general population may be exposed through dermal contact of consumer products containing this compound. (SRC)

Environmental Fate/Exposure Summary · 1 item

Dodecyl sulfate's production and use as a surfactant may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 3.2X10-8 mm Hg at 25 °C indicates dodecyl sulfate will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dodecyl sulfate will be removed from the atmosphere by wet and dry deposition. If released to soil, dodecyl sulfate is expected to have no mobility based upon an estimated Koc of 1.0X10+4. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole. If released into water, dodecyl sulfate is expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Dodecyl sulfate is readily biodegraded in water; 70% BOD and 69-93% COD removal have been observed after 2-4 weeks. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 71 suggests the potential for bioconcentration in aquatic organisms is moderate. Occupational exposure to dodecyl sulfate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where dodecyl sulfate is produced or used. The general population may be exposed through dermal contact of consumer products containing this compound. (SRC)

Non-Human Toxicity ValuesLD50 Rat oral 1300 mg/kg

Safety data

tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P280-P305+P351+P338
Hazardous Substances Data
151-41-7(Hazardous Substances Data)
Methods of Manufacturing
SULFATION OF 1-DODECANOL WITH SULFUR TRIOXIDE
General Manufacturing InformationSulfuric acid, monododecyl ester: ACTIVE

Applications

UsesPharmaceutic aid (surfactant).

Suppliers7 total

江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
上海辅欣医药科技有限公司021-50872116 13391048226 · [email protected]
河南伊诺凯新材料有限公司15670530983 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
东阳市求索医药科技有限公司17502510579 · [email protected]
武汉柔博医药化工有限公司027-027-87827088 18986164924 · [email protected]
上海臻励生物科技有限公司021-16621358918; 18516310516;16621358918;13045646768 · [email protected]

Additional notes

DefinitionChEBI: Dodecyl hydrogen sulfate is an alkyl sulfate. It is a conjugate acid of a dodecyl sulfate.