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ベヘン酸

Docosanoic Acid

HCID 8215
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
112-85-6
標準SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)O
InChIKey
UKMSUNONTOPOIO-UHFFFAOYSA-N
分子式
C22H44O2
平均分子量
340.6 g/mol
単同位体質量
340.33413064

概要

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

名称と識別子

優先名称
Docosanoic Acid
IUPAC
docosanoic acid
現地名
ベヘン酸
英語名
Docosanoic acid
分子式
C22H44O2
分子量
340.58

名称と別名

Docosanoic acidBehenic acid112-85-6N-DOCOSANOIC ACID1-Docosanoic acidHydrofol Acid 560Glycon B-70Hydrofol 2022-55Docosoic acidEdenor C 22-85RHystrene 5522Hystrene 9022
名称をさらに表示
ベヘン酸ベヘニン酸ドコサン酸N-ドコサン酸ベヘン酸標準品ドコサン酸, 菜種由来ドコサン酸標準品C22behenicdocosanoicB95EXL5NAA22SNAA222SCHacid B
Glycon B 70Prifrac 2989CRODACID BH390488X0ADTXSID3026930CHEBI:28941ORISTAR BAC22:0

データベース識別子

CAS
112-85-6
PubChem CID
8215
DTXSID
DTXSID3026930
ChEMBL
CHEMBL1173474
ChEBI
CHEBI:28941
UNII
H390488X0A
EC Number
204-010-8
Nikkaji
J2.461I

物性

構造計算による物性

XLogP
9.6
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
20
重原子数
24
形式電荷
0
複雑度
250

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids
Lipids · 2 件

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

Cosmetics · 2 件

Cosmetic ingredients (Behenic Acid) -> CIR (Cosmetic Ingredient Review)

Emulsifying

LogP9.910
Density0.8221 at 100 °C/4 °C
Color/Form · 2 件

Waxy solid

Needles

Solubility · 4 件

0.102 g are sol in 100 g of 90% ethanol at 17 °C;0.218 g are sol in 100 ml of 91.5% ethanol at 25 °C; 0.116 g are sol in 100 ml of 86.2% ethanol at 25 °C; 0.011 g are sol in 100 ml of 63.07% ethanol at 25 °C; 0.1922 g are sol in 100 g of ether at 16 °C

Slightly soluble in water, ethanol, ethyl ether

In water, 160 mg/L, temp not specified

1.6e-05 mg/mL

Boiling Point306 °C at 60 mm Hg
Melting Point · 2 件

79.95 °C

81 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

This chemical does not meet GHS hazard criteria for 97.4% (185 of 190) of all reports.

Not Classified

Aggregated GHS information provided per 190 reports by companies from 2 notifications to the ECHA C&L Inventory.

Not Classified

危険有害性情報

Regulatory Information · 5 件

Chemical: Docosanoic acid

Regulation (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)

REACH registered substance: Docosanoic acid (EC: 204-010-8)

Docosanoic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Docosanoic acid: Human health tier I assessment
Fire PotentialCombustible
Hazards Summary · 1 件

No data available on effects as an irritant or sensitizer; In 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 · 1 件

Organization for Economic Cooperation and Development; Screening 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 ChemicalChemical: Docosanoic acid

化学と産業

薬理情報

Tissue LocationsPlacenta
Cellular LocationsExtracellular

用途と製造

Uses · 6 件

CIR ingredient: Behenic Acid

Used in cosmetics, waxes, plasticizers, stabilizers and as a chemical intermediate; [HSDB] Used in lubricating oils and to retard solvent evaporation in paint removers; A minor constituent of most seed fats, animal milk fats, and marine animal oils; [Merck Index]

In lubricating oils, as solvent evaporation retarder in paint removers. Amide as anti-foam in the manufacture of detergents, in floor polishes, in dripless candles

Cosmetics; waxes; plasticizers; chemicals; stabilizers

CHEM INT FOR LITHIUM DOCOSANOATE (LITHIUM BEHENATE)

CHEM INT FOR SILVER DOCOSANOATE (SILVER BEHENATE)

Impurities(C14-C20) fatty acids ca. 11 %; C24 fatty acid ca. 2 %
U.S. Exports · 2 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

(1979) No Data

(1981) No Data

U.S. Production · 5 件

2023: 1,000,000 - <2,500,000 lb

(1977) AT LEAST 4.54X10+8 GRAMS

(1981) No Data

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5441]

Docosanoic acid is listed as a High Production Volume (HPV) chemical (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).

Consumer UsesLubricating agent
Industry Uses

関連反応

314 件
反応記録を作成
HRID 28323 の反応式
HRID 28323反応物としてuspto-grants-2008_09
HRID 30956 の反応式
HRID 30956生成物として反応物としてuspto-grants-2008_09
HRID 30957 の反応式
HRID 30957反応物としてuspto-grants-2008_09
HRID 33094 の反応式
HRID 33094生成物として反応物としてuspto-grants-2008_09
HRID 33095 の反応式
HRID 33095反応物としてuspto-grants-2008_09
HRID 33096 の反応式
HRID 33096生成物として反応物としてuspto-grants-2008_09
HRID 33097 の反応式
HRID 33097反応物としてuspto-grants-2008_09
HRID 47181 の反応式
HRID 47181反応物としてuspto-grants-2004_03
1 / 40 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Vapor Pressure
0.00000007 [mmHg]
Refractive IndexIndex of refraction: 1.4270 at 100 °C/D
Physical Description · 3 件

Other Solid; Large Crystals; Liquid; Other Solid; Liquid

White to cream or yellow solid; [CHEMINFO] White crystalline powder; [MSDSonline]

Solid

物理化学的性質

融点
72 · 72-80 °C(lit.)
沸点
306 °C · 306°C 60mm
比重(密度)
4100 · d4100 0.8221
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
100 · nD100 1.4270
闪点
306 °C/60mm · 306°C/60mm
貯蔵温度
Sealed in dry,Room Temperature
溶解性
50 mg/mL、透明 · クロロホルム:可溶50mg/mL、透明
外見
結晶性粉末
酸解離定数(Pka)
4.78 · 4.78±0.10(Predicted)
色
白色~やや黄色
臭い (Odor)
微かな匂い
由来生物
synthetic
水溶解度
DMF (~3 mg/ml)、熱メタノール、水 (0.15 mg/ml、25°C)、クロロホルム、エタノール (2.18 mg/ml、25°C) に可溶。
Merck
14 · 14,1023
BRN
1792887 · 1792887
Henry's Law Constant
9.5 · 9.5×10-2 mol/(m3Pa) at 25℃, Abraham (2003)
安定性
安定。可燃性。塩基、酸化剤、還元剤と相容れない。
化粧品成分の機能
界面活性剤 - 洗浄クレンジング界面活性剤 - 乳化剤不透明剤
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
4.121 · 4.121-9.91 at 25℃
CAS データベース
112 · 112-85-6(CAS DataBase Reference)
NISTの化学物質情報
Docosanoic acid(112-85-6)
EPAの化学物質情報
Docosanoic acid (112-85-6)

化学的性質

化学的特性white to cream crystals or powder

Hazard Classes and CategoriesNot Classified

安全と保護具

Disposal Methods · 2 件

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.

Dissolved or mixed the material with a combustible solvent and burned in a chemical incinerator equipped with an afterburner and scrubber.

毒性情報

Interactions · 1 件

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.

Ecotoxicity Values · 5 件

EC50 Selenastrum capricornutum (algae) >5.00 mg/L/72 hr; Conditions: static, 22.5 to 23.4 °C; Effect: growth rate. /Purity 96.5%/

EC50 Daphnia magna (water flea) >5.00 mg/L/48 hr; Conditions: static, 20.4 to 20.7 °C, pH=7.7 to 7.9; Effect: immobilization. /Purity 96.5%/

EC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 days; Conditions: semi-static (water renewal: 3 times a week), 19.9 to 20.6 °C, pH=7.0 to 8.0; Effect: reproduction. /Purity 96.5%/

LC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 days; Conditions: 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.

Environmental Fate · 3 件

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).

Food Survey ValuesDocosanoic acid was identified as a volatile component of roasted and boiled Chinese chestnuts (Castanea molissima)(1).
Milk ConcentrationsENVIRONMENTAL: Docosanoic acid is found as a minor constituent of animal milk fats(1).
Toxicity Summary · 3 件

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 qualifications

Oral 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 freshwater; Medaka 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 IntakeFatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.
Ecotoxicity Excerpts · 2 件

/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 · 1 件

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/g; samples collected were from trees characteristic of the Los Angeles, CA area(3).

Effluent Concentrations · 3 件

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 · 1 件

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 · 5 件

Minor constituent of most seed fats, animal milk fats and marine animal oils.

Occurs in bean oil

THE 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).

安全データ

wgk
-
tsca
TSCA listed
hs_code
2915900090
risk_code
36/37/38
化審法
(2)-608
safety_code
26-36/37/39-24/25
ストレージクラス
11 - Combustible Solids
有毒物質データの
112-85-6(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
火災[赤]=1
Monomers
Methods of Manufacturing · 2 件

Prepn from erucic acid by catalytic reduction

HYDROGENATION OF RAPESEED OR FISH OIL FOLLOWED BY HYDROLYSIS AND FRACTIONAL DISTILLATION; HYDROGENATION OF ERUCIC ACID (CIS-13-DOCOSENOIC ACID)

Formulations/PreparationsGrades: Technical, 99%
Household ProductsInformation on 33 consumer products that contain Behenic acid in the following categories is provided:
Use Classification · 3 件

EPA Safer Chemical Functional Use Classes -> Surfactants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Cosmetics -> Emulsifying

General Manufacturing Information · 3 件

All Other Chemical Product and Preparation Manufacturing

Docosanoic acid: ACTIVE

Straight chain saturated fatty acid. /From table/

応用分野 · 4 件

解説ベヘン酸,針状結晶.融点79.95 ℃,沸点306 ℃(8.0 kPa).d10040.8221.n100D1.4270.25 ℃ においてエタノールに約0.1%,16 ℃ においてエーテルに約0.2% 溶ける.森北出版「化学辞典(第2版)

用途有機合成原料。

使用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.

説明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.

調製方法

純化方法Crystallise the acid pKEst from ligroin. [Francis & Piper J Am Chem Soc 61 577 1939, Beilstein 2 IV 1290.]

上流・下流製品情報

下流製品

パルミトレイン酸ドコサン酸オクタデシルベヘン酸銀トリベヘニンベヘン酸 メチル1-ドコサノール

補足説明

定義本品は、次の化学式で表される脂肪酸である。