Docosanoic Acid

BEHENIC ACID · C22 · behenic · docosanoic · 1-Docosanoic acid · B95 · EXL5 · NAA22S

Identifikatoren & physikalische Daten

CAS No.	112-85-6
Summenformel	C22H44O2
Durchschnittliche Molmasse	340,6 g/mol
Monoisotopische Masse	340,33413065 g/mol
SMILES	CCCCCCCCCCCCCCCCCCCCCC(=O)O
InChIKey	UKMSUNONTOPOIO-UHFFFAOYSA-N
PubChem CID	8215
ChEMBL	CHEMBL1173474
ChEBI	CHEBI:28941
EC No.	204-010-8
DTXSID	DTXSID3026930

Chemische & physikalische Eigenschaften

XLogP	9,6
Polarare Oberfläche (TPSA)	37,3
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	20
Schwere Atome	24
Formalladung	0
Komplexität	250
Stoffklassen	Other Classes -> Organic Acids
Lipide	Lipids -> Unambiguous LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]
Kosmetika	Cosmetic ingredients (Behenic Acid) -> CIR (Cosmetic Ingredient Review)Emulsifying
LogP (Verteilungskoeffizient)	9.910
Dichte	0.8221 at 100 °C/4 °Cd4100 0.8221
Color/Form	Waxy solidNeedles
Löslichkeit	0.102 g are sol in 100 g of 90% ethanol at 17 °C0.218 g are sol in 100 ml of 91.5% ethanol at 25 °C0.116 g are sol in 100 ml of 86.2% ethanol at 25 °C0.011 g are sol in 100 ml of 63.07% ethanol at 25 °C0.1922 g are sol in 100 g of ether at 16 °CSlightly soluble in water, ethanol, ethyl etherIn water, 160 mg/L, temp not specified1.6e-05 mg/mLchloroform: soluble50mg/mL, clearSoluble in DMF (~3 mg/ml), hot methanol, water (0.15 mg/ml at 25°C), chloroform, and ethanol (2.18 mg/ml at 25°C).
Siedepunkt	306 °C at 60 mm Hg306°C 60mm
Schmelzpunkt	79.95 °C81 °C72-80 °C(lit.)
Dampfdruck	0.00000007 [mmHg]0Pa at 25℃
Brechungsindex	Index of refraction: 1.4270 at 100 °C/DnD100 1.4270
Physical Description	Other SolidLarge CrystalsLiquidWhite to cream or yellow solid[CHEMINFO] White crystalline powder[MSDSonline]
Flammpunkt	306°C/60mm
Lagerbedingungen	Sealed in dry,Room Temperature
Aggregatzustand	Crystalline Powder
pKa (Säurekonstante)	4.78±0.10(Predicted)
Farbe	White to slightly yellow
Geruch	faint odor
Biologische Quelle	synthetic
Merck	14,1023
BRN	1792887
Henry-Konstante	9.5×10-2 mol/(m3Pa) at 25℃, Abraham (2003)
Stabilität	Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.
Kosmetik-Inhaltsstoffe Funktionen	SURFACTANT - CLEANSINGCLEANSINGSURFACTANT - EMULSIFYINGOPACIFYING
InChI	1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)
InChIKey	UKMSUNONTOPOIO-UHFFFAOYSA-N
SMILES	CCCCCCCCCCCCCCCCCCCCCC(O)=O
LogP (Verteilungskoeffizient)	4.121-9.91 at 25℃
CAS Datenbank	112-85-6(CAS DataBase Reference)
NIST chemische Informationen	Docosanoic acid(112-85-6)
EPA chemische Informationen	Docosanoic acid (112-85-6)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 97.4% (185 of 190) of all reports.Not ClassifiedAggregated GHS information provided per 190 reports by companies from 2 notifications to the ECHA C&L Inventory.
Regulatorische Informationen	Chemical: Docosanoic acidRegulation (EC) No 178/2002 (amended)Docosanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Docosanoic acid 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)Status: Active Update: 29-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14201Docosanoic acid: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - Docosanoic acid: Human health tier I assessment
Brandpotenzial	Combustible
Gefahrenübersicht	No data available on effects as an irritant or sensitizerIn a feeding study of rats at doses up to 1000 mg/kg/day for 42 days, negative for toxic effects and no reproductive or developmental adverse effects[OECD SIDS: Docosanoic acid - 2001] An irritant[MSDSonline]
Special Reports	Organization for Economic Cooperation and DevelopmentScreening Information Data Set for Docosanoic acid (CAS #112-85-6) (November 6 - 9, 2001). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of January 24, 2008.
EPA Safer Chemical	Chemical: Docosanoic acid
Hazard Classes and Categories	Not Classified
Entsorgungsverfahren	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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Dissolved or mixed the material with a combustible solvent and burned in a chemical incinerator equipped with an afterburner and scrubber.
Wechselwirkungen	THE BLOOD PLATELET AGGREGATING EFFECT OF BEHENIC ACID ON WASHED PIG BLOOD PLATELETS WAS ENHANCED BY THE ADDITION OF CALCIUM IONS. LINOLENIC ACID COMPLETELY INHIBITED THE EFFECT OF BEHENIC ACID WHEN BOTH WERE ADDED IN EQUIMOLAR CONCENTRATIONS.
Ökotoxizitätswerte	EC50 Selenastrum capricornutum (algae) >5.00 mg/L/72 hrConditions: static, 22.5 to 23.4 °CEffect: growth rate. /Purity 96.5%/EC50 Daphnia magna (water flea) >5.00 mg/L/48 hrConditions: static, 20.4 to 20.7 °C, pH=7.7 to 7.9Effect: immobilization. /Purity 96.5%/EC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 daysConditions: semi-static (water renewal: 3 times a week), 19.9 to 20.6 °C, pH=7.0 to 8.0Effect: reproduction. /Purity 96.5%/LC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 daysConditions: semi-static (water renewal: 3 times a week), 19.9 to 20.6 °C, pH=7.0 to 8.0. /Purity 96.5%/For more Ecotoxicity Values (Complete) data for DOCOSANOIC ACID (6 total), please visit the HSDB record page.
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). Docosanoic is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-8 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation of 69% of the theoretical BOD using a modified closed bottle Blok test employing a sewage inoculum incubated 28 days(6) suggests that biodegadation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5 for the free acid(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 4.7(3) indicates docosanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 9.91(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A half life of 1.7 days in freshwater after a 29 days(8) suggests 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), docosanoic acid, which has an estimated vapor pressure of 7.1X10-8 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 docosanoic acid 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 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase docosanoic acid may be removed from the air by wet or dry deposition(SRC). Docosanoic acid 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).
Lebensmitteluntersuchungswerte	Docosanoic acid was identified as a volatile component of roasted and boiled Chinese chestnuts (Castanea molissima)(1).
Milk Concentrations	ENVIRONMENTAL: Docosanoic acid is found as a minor constituent of animal milk fats(1).
Toxizitätsübersicht	The CIR Expert Panel concluded that the following ingredients are safe in the present practices of use andconcentration described in the safety assessment when formulated to be non-irritating and non-sensitizing, which may be basedon a QRA...Behenic Acid...Safe for use in cosmetics, with qualificationsOral LD50 value of docosanoic acid for rats is greater than 2,000 mg/kg. There are no available data for irritation and sensitization. In an oral study using the OECD combined repeated dose and reproductive/developmental toxicity test [OECD TG 422], docosanoic acid was administered to rats at doses of 0, 100, 300, 1,000 mg/kg/day for at least 42 days . No deaths occurred and also no substance related toxic effects were observed in any parameters. Therefore, the NOAEL is considered to be 1,000 mg/kg/day for both repeated dose toxicity and reproductive/developmental toxicity. The chemical was negative in both a bacterial mutation test [OECD TG 471, 472] and a chromosomal aberration test in vitro [OECD TG 473]. ... Acute toxicity values of docosanoic acid on alga (Selenastrum capricornutum), aquatic invertebrate (Daphnia magna) or fish (Oryzias latipes) are greater than its water solubility (0.016 mg/L). The NOEC in a 21-day reproduction test with Daphnia magna is also greater than its water solubility. No significant effects are observed in any tests conducted at extremely high concentrations by using dispersant under OECD test guidelines [TG201, 202, 203, 204, or 211]. There is information that some fatty acids with shorter carbon chain caused no mortality at saturated concentration in certain aquatic organisms (gammarus in freshwaterMedaka in seawater condition). Considering from these data and additional information, it is reasonable to assume that docosanoic acid is not toxic to aquatic organisms at the concentration less than its water solubility (0.016 mg/L). A PNEC is not calculated since NOEC values obtained are above the water solubility of the substance.
Average Daily Intake	Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.
Ökotoxizitätsauszüge	/AQUATIC SPECIES/ In a chronic toxicity test with Daphnia magna, conducted at 0.30, 0.55 and 1.00 mg/L under semi-static conditions (water renewal: 3 times a week), the measured concentrations in groups tested at 21 day were different over 20% from their corresponding nominal concentration. Thus, the concentrations were expressed using time-weighted averages: 0.24, 0.49 and 0.84 mg/L, respectively. The parental mortalities observed in controls and treated groups were within the range of 20% and no effects by dispersant were observed. EC50 and NOEC values in this chronic toxicity test to Daphnia magna on reproduction were greater than 0.84 mg/L./AQUATIC SPECIES/ Toxicity studies of docosanoic acid have been conducted using dispersant in a limited number of representative aquatic organisms: algae (Selenastrum capricornutum), aquatic invertebrates (Daphnia magna), and fish (Oryzias latipes) ... In all tests, no significant effect was observed at considerably higher concentration than its water solubility (0.016 mg/L).
Plant Concentrations	Docosanoic acid is found as a minor constituent of most seed fats and in large amounts in jamba oil, mustard seed oil and rape oil(1). Docosanoic acid occurs in bean oil, hydrogenated mustard oil, and rapeseed oil(2). Docosanoic acid was found in fine particulate abrasion products from green leaves at a concn of 152.2 ug/g and from dead leaves at a concn of 212.4 ug/gsamples collected were from trees characteristic of the Los Angeles, CA area(3).
Effluent Concentrations	Water samples taken from the effluent of a kraft paper mill located on the shore of Lake Saimaa, Lappeenranta, Finland were found to contain docosanoic acid concns ranging from 1 to 37 ug/L over a 9 day period(1). Docosanoic acid was identified in a tire manufacturing plant wastewater at 1 mg/L(2).Docosanoic acid was found in candle smoke from paraffin and beeswax at 0.15 and 1.21 mg/g of organic compounds(1). Docosanoic acid was found in wood smoke from yellow poplar, white ash, sweet gum, mockernut hickory, loblolly pine, and slash pine(2). Docosanoic acid was detected in wood smoke from pine, oak and synthetic logs at 7.98, 4.63 and 0.99 mg/kg of wood burnt(3). Docosanoic acid was found at 20.8, 7.61 and 5.09 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase(4). Docosanoic acid was found in extract from a pine wood burning campfire at 628 ng/g(5). Docosanoic acid was found at 17 ug/g from heated roofing tar pot fumes(6).Docosanoic acid was not detected in tire wear particles, and in brake lining particles and road dust particles at concns of 2.1 ug/g and 70.2 ug/g of particle sample, respectively(1). Docosanoic acid was emitted at 350 ug/kg of cooked meat in the particulate phase(2). Fine particle emission of docosanoic acid from a natural gas-fired water heater and a natural gas-fired space heater were not detected(3).
Soil Adsorption/Mobility	Using a structure estimation method based on molecular connectivity indices(1), the Koc of undissociated docosanoic acid can be estimated to be 1.4X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Natural Pollution Sources	Minor constituent of most seed fats, animal milk fats and marine animal oils.Occurs in bean oilTHE HIGHEST CONCENTRATION OF BEHENIC ACID WAS FOUND IN GARCINIA MANGOSTANA AND VENTILAGO MADRASPATANA SEEDS.BEHENIC ACID (2.62%) WAS ISOLATED FROM THE OIL OBTAINED FROM THE MEDICINAL PLANT ERYTHRINA SUBEROSA ROXB SEEDS.Docosanoic acid is a carboxylic acid that is also known as a fatty acid because fatty acids were first isolated by the hydrolysis of naturally occurring fats(1). Fatty acids are widely distributed in nature as components of animal and vegetable fats(2) including lipids such as oils and fats, waxes, sterol esters and other minor compounds(1).
Wassergefährdungsklasse (WGK)	-
TSCA-Inventar-Status	TSCA listed
Zollcode	29159000
R-Sätze (R)	36/37/38
Sicherheitshinweise (S)	26-36/37/39-24/25
Lagerklasse	11 - Combustible Solids
Gefahrstoffdaten	112-85-6(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Docosanoic acid is a long-chain fatty acid,it has the following purposes: Waxes, textiles, pharmaceuticals, emulsifiers, and personal care products, lubricants, esters, chemical synthesis, and specialties.

Beschreibung

Docosanoic acid is a straight-chain, C22, long-chain saturated fatty acid. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a behenate.