1-Dodecanol

HCID 8193CAS 112-53-8

Grundinformationen

Standard-SMILES
CCCCCCCCCCCCO
InChIKey
LQZZUXJYWNFBMV-UHFFFAOYSA-N
Summenformel
C12H26O
Durchschnittliche Molmasse
186,33 g/mol
Monoisotopische Masse
186,19836545

Namen und Bezeichner

Bevorzugter Name
1-Dodecanol
IUPAC
dodecan-1-ol
Englischer Name
1-Dodecanol
Summenformel
C12H26O
Molmasse
186.33

Namen und Synonyme

1-DODECANOLDodecan-1-olDodecyl alcohol112-53-8Lauryl alcoholn-Dodecyl alcoholLauric alcoholLaurinic alcoholUndecyl carbinolDodecylalcohol1-HydroxydodecanePisol
Weitere Namen anzeigen
Fatty alcoholDODECANOLlauryldodecylFEMA 2617
1-Dodecyl alcoholn-Dodecan-1-olDuodecyl alcoholLorol 5Lorol 7Lauryl 24Alcohol C-12Alfol 12

Datenbank-Bezeichner

CAS
112-53-8、27342-88-7、68551-07-5
PubChem CID
8193
DTXSID
DTXSID5026918
ChEMBL
CHEMBL24722
ChEBI
CHEBI:28878
UNII
178A96NLP2
EC Number
203-982-0
Nikkaji
J1.505I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,1
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
10
Schwere Atome
13

Experimentelle und physikochemische Eigenschaften

LogP · 3 Einträge

log Kow = 5.13

5.13

5.4

Odor · 2 Einträge

CHARACTERISTIC FATTY ODOR; UNPLEASANT AT HIGH CONCN BUT DELICATE & FLORAL ON DILUTION

Fatty repulsive odor

TasteFATTY, WAXY FLAVOR
Density · 6 Einträge

0.831 at 75.2 °F (USCG, 1999) - Less dense than water; will float

0.8309 at 24 °C/4 °C

0.8309 AT 24 °C/4 °C

Density (at 24 °C): 0.83 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

0.830-0.836

Viscosity · 2 Einträge

18.8 mPa-s at 20 °C

21.7 mm²/s at 20 °C

Color/Form · 4 Einträge

Leaflets from dilute alcohol

COLORLESS LIQ AT ROOM TEMP; CRYSTALLINE OR FLAKES BELOW 20 °C

Colorless solid

CRYSTALLINE SOLID

Physikochemische Eigenschaften

Schmelzpunkt
22 · 22-26 °C(lit.)
Siedepunkt
260 · 260-262 °C(lit.)
Dichte
0.833 g/mL · 0.833 g/mL at 25 °C(lit.)
Dampfdichte
7.4 · 7.4 (vs air)
Dampfdruck
0.1 mm · 0.1 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.442(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 2.2% (85 of 3888) of reports.

Warning

H319 (83.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H400 (85.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (14%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H411 (24.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3888 reports by companies from 38 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 85 of 3888 reports by companies.;There are 37 notifications provided by 3803 of 3888 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 1-Dodecanol

1-Dodecanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Dodecanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2008/127, Reg. (EU) 2017/195, Reg. (EU) 2021/745, Reg. (EU) 2022/1251, Reg. (EU) No 540/2011, Reg. (EU) No 918/2014, Reg. (EU)2020/1160

Status: Active Update: 09-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15424

1-Dodecanol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1-Dodecanol: Human health tier I assessment
DOT LabelClass 9
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, Capacitor, asymmetric, be aware of possible short circuiting as this product is transported in a charged state. Polymeric beads, expandable (UN2211) may evolve flammable vapours. (ERG, 2024)

Combustible.

Fire PotentialCombustible when it is exposed to heat or flame.
Health HazardsLiquid will cause burning of the eyes and may irritate skin. (USCG, 1999)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.;Fire Extinguishing Agents: Alcohol foam, carbon dioxide, dry chemical (USCG, 1999)

Use water, dry powder, carbon dioxide, alcohol-resistant foam.

First Aid Measures · 4 Einträge

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Rest. Do NOT induce vomiting. Seek medical attention if you feel unwell.

First AidSKIN OR EYES: wash exposed areas with water. (USCG, 1999)
Safe StorageCool. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Fire Fighting Procedures · 2 Einträge

Wear self contained breathing apparatus for fire fighting if necessary.

Alcohol foam, carbon dioxide, dry chemical. Water or foam may cause frothing. Water may be ineffective on fire. Cool exposed containers with water.

Storage ConditionsKeep tightly closed. Store in a cool dry place.

Toxikologische Informationen

Body Burden1-Dodecanol was qualitatively detected in expired air of humans having diabetic conditions(1); it was not detected (detection limit not reported) in expired air of non-diabetic humans(1).
Interactions · 2 Einträge

Nutritional encephalomalacia induced by lauryl alcohol could be completely prevented by dietary supplementation of dl-alpha-tocopheryl acetate.

IN PRESENCE OF DODECANOL, DEPRESSION OF AMPLITUDE OF COMPD ACTION POTENTIAL BY BUTANOL (30 MMOL) WAS INCR.

Ecotoxicity Values · 5 Einträge

LC50; Species: Pimephales promelas (Fathead minnow) weight 0.12 g; Conditions: flow-through bioassay, water hardness 45.5 mg/L CaCO3, temp: 25 +/- 1 °C, pH 7.5, dissolved oxygen >60% of saturation; Concentration: 1.01 mg/L for 96 hr

LC50; Species: Nitocra spinipes (Harpacticoid copepod); Conditions: static; Concentration: 0.9 mg/L for 96 hr (95% confidence limit: 0.8-1.2 mg/L) /formulated product/

EC50; Species: Brachionus calyciflorus (Rotifer); Conditions: static; Concentration: 810 ug/L for 48 hr (95% confidence limit: 767-1020 ug/L); Effect: decreased distance moved, change in direct movement

EC50; Species: Tetrahymena pyriformis (Ciliate); Conditions: static; Concentration: 1.58 mg/L for 48 hr; Effect: decreased population growth /formulated product/

LC50; Species: Lepomis macrochiris (Bluegill sunfish); Conditions: static bioassay; Concentration: 894 mg/L for 96 hr. /Alcohol mixture containing 66% dodecanol/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), reported Koc values of 2042-3388 in humic acid(2), indicate that 1-dodecanol is expected to have slight mobility in soil(SRC). Volatilization of 1-dodecanol from moist soil surfaces is expected(SRC) given a Henry's Law constant of 5.19X10-5 atm-cu m/mole(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Dodecanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.48X10-4 mm Hg at 25 °C(4). Theoretical BOD values using standard 5-day aerobic sewage tests ranged from 20-29.7%(5-7) indicate that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 7700 in suspended solids and 2337-11,184 in sediment(2), indicate that 1-dodecanol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 5.19X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 27 hours and 12 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 volatilization half-life from a model pond is about 11 months when adsorption is considered(5). 1-Dodecanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 48(SRC), from its log Kow of 5.13(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Theoretical BOD values, using standard 5-day aerobic sewage tests ranged from 20-29.7%(9-11), indicate that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-dodecanol, which has a vapor pressure of 8.48X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-dodecanol 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 21 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Dodecanol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values1-Dodecanol was qualitatively detected as a volatile flavor component of Idaho Russet Burbank baked potatoes(1) and in beef(2). 1-Dodecanol has been detected in beer, wine and spirits(3).
Adverse Effects · 2 Einträge

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Regulatorische Informationen

Regulatory Information · 5 Einträge

Chemical: 1-Dodecanol

1-Dodecanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Dodecanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2008/127, Reg. (EU) 2017/195, Reg. (EU) 2021/745, Reg. (EU) 2022/1251, Reg. (EU) No 540/2011, Reg. (EU) No 918/2014, Reg. (EU)2020/1160

Status: Active Update: 09-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15424

1-Dodecanol: Does not have an individual approval but may be used under an appropriate group standard

FDA Requirements · 2 Einträge

Lauryl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Lauryl alcohol is an indirect food additive for use as a component of adhesives.

FIFRA Requirements · 4 Einträge

Residues of lauryl alcohol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: surfactant.

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether or not products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing aliphatic alcohols as an active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing aliphatic alcohols (C6 - C16). The Agency has completed its assessment of the human health and ecological risks associated with the use of pesticide products containing aliphatic alcohols (C6 - C16). The Agency has determined that aliphatic alcohol-containing products are eligible for reregistration provided that label amendments are made as outlined in Chapter V. ... The Agency has identified eye-irritation concerns that warrant specific label language concerning personal protective equipment (PPE) and the length of restricted-entry intervals after application for tobacco uses of the aliphatic alcohols (C6 - C16). If all changes outlined in this document are incorporated into the product labels, the eye-irritation concerns will have been mitigated. Should a registrant fail to implement any of the reregistration requirements identified in this document, the Agency may take regulatory action to address these concerns.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 001509; Type of Pesticide: biological - insect pheromone; Use Site: food use; Year: 1992.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Decanol is found on List D. Case No: 4004; Pesticide type: Insecticide, herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Decanol; Data Call-in (DCI) Date(s): 10/01/93; AI Status: All products containing this pesticide that were subject to reregistration have been cancelled. However, recently registered products contain this pesticide as a new active ingredient.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 3077 9/PG 3
hs_code
29051700
RTECS-Nr.
JR5775000
risk_code
38-50-50/53-36/38-36/37/38

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Frog liver microsomes catalyzed the hydroxylation of 1-dodecanol into the corresponding omega- and (omega-1)-hydroxy derivatives. The hydroxylation rate for 1-dodecanol was much lower than that for lauric acid. Both NADPH and O2 were required for hydroxylation activity. NADH had no effect on the hydroxylation. The hydroxylating system was inhibited 49% by CO at a CO:O2 ratio of 4.0. The formation of omega-hydroxydodecanol was more sharply inhibited by CO than was the formation of (omega-1)-hydroxydodecanol, implying that more than one cytochrome P-450 was involved in the hydroxylation of 1-dodecanol and that CO has a higher affinity for the P-450 catalyzing the omega-hydroxylation. The formation of laurate during the incubation of 1-dodecanol with frog liver microsomes suggests that a fatty alcohol oxidation system is also present in the microsomes. NAD+ was the most effective cofactor for the oxidation of 1-dodecanol and NADP+ had a little effect. Pyrazole (an inhibitor of alcohol dehydrogenase) had a slight inhibitory effect on the oxidation and sodium azide (an inhibitor of catalase) had no effect.

The liver microsomes of the Mongolian gerbil Meriones unguiculatus catalyzed the hydroxylation of various saturated fatty acids (C8-C18), alcohols (C12 and C16) and hydrocarbon (C12) to the corresponding omega- and (omega-1)-hydroxy derivatives. Lauric acid was hydroxylated most effectively among saturated fatty acids and the order of activity as hydroxylation substrates was C12 greater than C14 greater than C13 greater than C16 greater than C10 greater than C18 greater than C8. The specific activity of laurate hydroxylation (5.99 nmol/mg microsomal protein/min) in gerbil liver microsomes was higher than that observed in other species. 1-Dodecanol was also hydroxylated very effectively (4.58 nmol/mg microsomal protein/min) by gerbil liver microsomes, but in general the hydroxylation rates for fatty alcohols were much lower than those for the corresponding acids.

Absorption, Distribution and Excretion · 1 Eintrag

After 24-hr covered contact with the skin of mice, about 95% of a 100-uL dose of 0.5% 1-dodecanol in triethyl citrate remained on the skin. A small proportion, 0.1%, was recovered in the feces and urine, 0.13% was recovered from the body, and 2.61% was excreted in the air. These data indicate a low amount of dermal uptake.

Cellular LocationsExtracellular;Membrane

Verwendung und Herstellung

Uses · 6 Einträge

Used to manufacture sulfuric acid esters (wetting agents) and in synthetic detergents, lube additives, pharmaceuticals, rubber, textiles, and perfumes; Also used as a flavoring agent and as a foam stabilizer for alcohol sulfate surfactants; [HSDB] Used to make surfactants for detergents, cleaning products, shampoos, cosmetics, lubricants, wetting agents, emulsifiers, dispersing agents, and antioxidants; Also used to make biocides and disinfectants; 1-Dodecanol is used in foam control, aluminum rolling, metalworking, and in the rubber, textiles, cosmetics, and perfume industries; Also used as a froth flotation agent and a flavoring ingredient in non-alcoholic beverages, ice cream, candy, baked goods, chewing gum, and syrups; [CHEMINFO] Used as Lepidoptera pheromone in apple and pear orchards; [EPA]

Aluminum Producing [Category: Industry];Metal Machining [Category: Heat or Machine];Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

Used to make detergents, sulfonic acid esters (wetting agents), thiodipropionate, lauryl chloride, specialty ethoxylates, sulfate defoamers, lube additives, pharmaceuticals, rubbers, textiles, perfumes, and foaming agents; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

For 1-dodecanol (USEPA/OPP Pesticide Code: 001509 ) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Manufacture of sulfuric acid esters which are used as wetting agents.

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production · 6 Einträge

2023: 50,000,000 - <100,000,000 lb;2022: 100,000,000 - <250,000,000 lb;2021: 100,000,000 - <250,000,000 lb;2020: 70,000,000 - <85,000,000 lb

(1972) 2.2X10+10 G (INCL C10+ LINEAR ALCOHOLS)

(1975) 1.01X10+11 G (INCL HIGHER ALCOHOLS)

(1986) >10 million-50 million pounds

(1990) >50 million-100 million pounds

For more U.S. Production (Complete) data for 1-DODECANOL (12 total), please visit the HSDB record page.

Consumption Patterns · 2 Einträge

Use as a chemical intermediate for n-dodecyl sulfate salts is believed to consume the largest quantity of 1-dodecanol; production of ethoxylated 1-dodecanol is probably the next largest market (1976)

In the U.S.A. approximately 20,000 lbs/year are used in fragrances, and some typical concentrations reported in personal care products include soaps (0.01 - 0.09%), detergents (0.002 - 0.018%), lotions and creams (0.005 - 0.02%) and perfumes (0.09 - 0.25%).

Consumer UsesLubricating agent;Cleaning agent;Not Known or Reasonably Ascertainable;Emulsifier
Anwendungen · 2 Einträge

OccurrenceReported found in the oil of Mexican lime and in the oil from flowers of Furcraea gigantean. Also reported found in apple, banana, sour cherry, citrus peel oils, melon, pineapple, potato, thymus, cheeses, butter, milk powder, chicken and beef fat, cooked pork, beer, whiskies, white wine, peanuts, beans, mushrooms, mango, coriander seed and leaf, rice, Bourbon vanilla, endive, crab, clam, Cape gooseberry, pawpaw and maté.

Verwenden1-Dodecanol is used in chemical formulations for a variety of purposes, including as an emulsion stabilizer, a skin-conditioning emollient, and a viscosity-increasing agent.

Darstellung

synthetischeCommercially 1-Dodecanol may be prepared by hydrogenation of lauric acid; normally employed as a replacement for the corresponding aldehyde.

Anbieter2 Anbieter

HONEST JOY HOLDINGS LIMITED[email protected]
Portail Substances Chimiques[email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 1-Dodecanol is a fatty alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certa n moths whose larvae destroy crops.

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