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1-エイコサノール

1-Eicosanol

HCID 12404
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
28679-05-2
標準SMILES
CCCCCCCCCCCCCCCCCCCCO
InChIKey
BTFJIXJJCSYFAL-UHFFFAOYSA-N
分子式
C20H42O
平均分子量
298.5 g/mol
単同位体質量
298.32356596

概要

Icosan-1-ol is a long-chain primary fatty alcohol that is icosane in which one of the terminal methyl hydrogens is replaced by a hydroxy group. It has a role as a volatile oil component, a plant metabolite and a human metabolite. It is an icosanol and a long-chain primary fatty alcohol.

名称と識別子

優先名称
1-Eicosanol
IUPAC
icosan-1-ol
現地名
1-エイコサノール
英語名
1-Eicosanol
分子式
C20H42O
分子量
298.55

名称と別名

1-EICOSANOLIcosan-1-ol629-96-9Arachidyl alcoholArachidic alcoholArachic alcoholEicosyl alcoholN-Eicosanol1-IcosanolN-1-EicosanolPri-N-eicosyl alcoholNSC 120887
名称をさらに表示
1-エイコサノール1-イコサノールエイコシルアルコールアラキジルアルコールアラキンアルコールイコシルアルコールイコサン-1-オールN-エイコシルアルコールアラキルアルコールエイコサノール1エイコサノル1‐エイコサノールエイコサン-1-オールアイコサン-1-オールアラキジル アルコール(EICOSAエイコサノールEICOSANOLEICOSAN-1-OLIcosyl AlcoholARACHYL ALCOHOLIcosanolARACHIDYL
HSDB 57311QR1QRA9BUEINECS 211-119-4AI3-36485NSC-1208871-EICOSANOL [HSDB]DTXSID0027272CHEBI:75627

データベース識別子

CAS
28679-05-2、629-96-9

物性

構造計算による物性

XLogP
9.5
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
18
重原子数
21
形式電荷
0
複雑度
167

実験および物理化学的性質

LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
PolymersOther Classes -> Alcohols and Polyols, Other
CosmeticsEmollient
Density0.8405 at 20 °C/4 °C
Color/Form · 2 件

White, wax-like solid

WAX FROM ALC AND CRYSTALS FROM CHLOROFORM

Solubility · 2 件

Very soluble in acetone; soluble in petroleum ether; slightly soluble in ethanol, chloroform

Soluble in hot benzene

Flash Point195 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point309 °C at 750 mm Hg; 222 °C at 3 mm Hg
Melting Point · 2 件

66.1 °C

66.1 °C

Vapor Pressure0.00000004 [mmHg]
Refractive Index

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 · 5 件

This chemical does not meet GHS hazard criteria for 74.9% (347 of 463) of all reports.

Warning

H319 (19.9%): 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 463 reports by companies from 11 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Chemical: 1-Eicosanol

1-Eicosanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Eicosanol 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: 31-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14380

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

Other Safety InformationIMAP assessments - 1-Eicosanol: Human health tier I assessment
Hazards Summary · 1 件

A mild skin and eye irritant; [HSDB] Aliphatic alcohols are metabolized and eliminated efficiently; Not skin sensitizers; May have low-grade liver effects; CNS depression seen in shorter chain alcohols, e.g., 1-hexanol and 1-octanol; [Reference #1] May cause irritation; [MSDSonline]

EPA Safer ChemicalChemical: 1-Eicosanol
Hazard Classes and CategoriesEye Irrit. 2A (19.9%)
Skin, Eye, and Respiratory IrritationsEicosanol /causes/ slight skin and eye irritation. /From table/ /Mixed isomers/

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

The lipids of the Gram-negative marine bacterium Marinobacter hydrocarbonoclasticus, cultivated in synthetic seawater on a single carbon source, acetate or n-icosane, were isolated, purified and their structures determined. Three different pools of lipids were isolated according to the sequential procedure used: "unbound" lipids extractable by solvents, lipids released under basic conditions ("ester bound") and lipids released by acid hydrolysis ("amide bound"). Even-carbon-numbered, n-fatty acids were identified in the "unbound" lipids of both the acetate and n-icosane cultures. In addition to these compounds, n-icosane induced the formation of n-icosan-1-ol and n-icos-11-en-1-ol, and also of a series of ß-hydroxy acids ranging from C12 to C20. In the "ester bound" lipids of the two cultures, short and long chain fatty acids were identified together with the ß-hydroxy C12:0 acid. This hydroxy acid was, by far, the major compound identified in the "amide bound" lipids of the two cultures. Comparison of the analytical data for the two cultures, and the differences in composition thus observed for the "unbound" pool, suggest the following metabolic pathway for n-icosane: hydroxylation to the C20 primary alcohol, transformation into the C20 ß-hydroxy acid and subsequent degradation into lower homologues. In sharp contrast, lipids from the "ester bound" and "amide bound" pools were quite unaffected by the change of nutrient. Lipids from Escherichia coli were also examined in the same manner. The results are discussed in terms of geochemical implications, relative to the presence of "unbound" ß-hydroxy acids in particulate matter and sediments.

Cellular LocationsExtracellular

用途と製造

Uses · 4 件

Used in lubricants, rubber, plastics, and textiles; Used as an emulsion stabilizer and viscosity increasing agent; [HSDB]

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

Lubricants, rubber, plastics, textiles; research

Emulsion stabilizer; viscosity increasing agent - aqueous; viscosity increasing agent - nonaqueous

U.S. Production · 6 件

関連反応

7 件
反応記録を作成
HRID 97957 の反応式
HRID 97957反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 135937 の反応式
HRID 135937反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 247719 の反応式
HRID 247719反応物としてuspto-grants-1987_11
HRID 414169 の反応式
HRID 414169反応物としてuspto-grants-1988_12
HRID 583018 の反応式
HRID 583018反応物としてuspto-grants-1999_07
HRID 814789 の反応式
HRID 814789反応物としてTest data from https://doi.org/10.1039/C8SC04228D
HRID 1377380 の反応式
HRID 1377380反応物としてuspto-grants-1997_09

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
PubChem CID
12404
DTXSID
DTXSID0027272
ChEMBL
CHEMBL451717
ChEBI
CHEBI:75627
UNII
1QR1QRA9BU
EC Number
211-119-4
Nikkaji
J11.549E
Index of refraction = 1.450 at 20 °C/D

物理化学的性質

融点
62 · 62-65 °C(lit.)
沸点
220 · 220-225°C 3mm
比重(密度)
0 · 0,841 g/cm3
蒸気密度
7.4 · 7.4 (vs air)
蒸気圧
0.1 mm · <0.1 mm Hg ( 20 °C)
屈折率
1.435 · 1.4350
闪点
195 °C · 195°C
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.001 g/L · 水:微溶 0.001g/L at 23℃
酸解離定数(Pka)
15.2 · 15.20±0.10(Predicted)
外見
ペレット、粉末またはチャンク
色
白い
水溶解度
水に不溶。
BRN
1705104 · 1705104
Henry's Law Constant
4.7 · 4.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
化粧品成分の機能
乳化安定剤粘度制御皮膚コンディショニング剤 - 保湿剤
InChI
1S/C20H42O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21/h21H,2-20H2,1H3
InChIKey
BTFJIXJJCSYFAL-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCCCCCCCCO
LogP
8.3 · 8.3
CAS データベース
629 · 629-96-9(CAS DataBase Reference)
NISTの化学物質情報
1 · 1-Eicosanol(629-96-9)
EPAの化学物質情報
1 · 1-Eicosanol (629-96-9)

化学的性質

化学的特性white fluffy crystalline powder

安全と保護具

Disposal Methods · 1 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.

毒性情報

Interactions · 3 件

Long-chain fatty acids and alcohols, including 1-eicosanol, inhibit specific binding of (3)H-labeled ouabain to a particulate fraction from dog heart. The magnitude of inhibition increases with chain length, reaching a maximum with lauric acid, myristoleic acid, and decanol in a series of saturated fatty acids, unsaturated fatty acids, and alcohols, respectively, followed by a decline with longer chain members of homologous series.

... None of these alcohols alone increased plasma alanine aminotransferase (ALT) or aspartate aminotransferase (AST) significantly, whereas CCl4 or CHCl3 administration to alcohol-treated animals resulted in significant elevation of plasma transaminases. Eicosanol (20-carbon alcohol) did not potentiate the toxicity of either halomethane. Methanol, ethanol, isopropanol, and decanol in combination with CCl4 caused massive liver damage but failed to augment CCl4 lethality. t-Butanol, pentanol, hexanol, and octanol significantly decreased the LD50 of CCl4. The hepatotoxic effects of CHCl3 were potentiated by all of the alcohols and the LD50s were also decreased significantly. Alcohol-potentiated CHCl3 toxicity was greater than the toxicity of CCl4.

The present ... experiments were designed to test: (i) whether a single subtoxic dose of alcohol can potentiate /carbon tetrachloride/ CCl4 and /chloroform/ CHCl3 hepatoxicity, and (ii) whether this potentiation leads to greater animal lethality. Selected members of a homologous series of straight chain alcohols were chosen for this study. Methanol, ethanol, isopropanol, t-butanol, pentanol, hexanol, octanol, decanol, and eicosanol at equimolar doses (10 mmol/kg) were tested in the present investigation. Each alcohol was administered orally to male Sprague-Dawley rats (175 to 250 g) 18 hr prior to a single oral administration of CCl4 or CHCl3. Liver injury was assessed by plasma transaminases (alanine aminotransferase, ALT; aspartate aminotransferase, AST) and histopathological examination of liver sections 24 hr after the halomethane treatment. None of these alcohols alone increased plasma ALT or AST significantly, whereas CCl4 or CHCl3 administration to alcohol-treated animals resulted in significant elevation of plasma transaminases. Eicosanol (20-carbon alcohol) did not potentiate the toxicity of either halomethane. Methanol, ethanol, isopropanol, and decanol in combination with CCl4 caused massive liver damage but failed to augment CCl4 lethality. t-Butanol, pentanol, hexanol, and octanol significantly decreased the LD50 of CCl4 .... On a comparative basis, alcohol-potentiated CHCl3 toxicity was greater than the toxicity of CCl4.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.4X10+4(SRC), determined from a structure estimation method(2), indicates that 1-eicosanol is expected to be immobile in soil(SRC). Volatilization of 1-eicosanol from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 9.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1-Eicosanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.5X10-8 mm Hg(4). 1-Eicosanol is expected to biodegrade rapidly(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.4X10+4(SRC), determined from a structure estimation method(2), indicates that 1-eicosanol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 2.1X10-5 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 7 hours and 7 days, respectively(SRC). However, adsorption to suspended solids is expected to attenuate volatilization(SRC). The estimated volatilization half-life from a model pond is 16 months if adsorption is considered(9). According to a classification scheme(5), an estimated BCF of 10(SRC), from an estimated log Kow of 8.7(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1-Eicosanol is expected to biodegrade rapidly(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-eicosanol, which has an estimated vapor pressure of 4.5X10-8 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 1-eicosanol 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 13 hours(SRC), calculated from its rate constant of 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-eicosanol may be removed from the air by wet or dry deposition(SRC).

Plant Concentrations1-Eicosanol emission rates from green leaf composite samples and dead leaves were 34 ug/g and 17 ug/g, respectively(1).
Effluent Concentrations · 1 件

Emission rates from wood smoke in mg/g of organic carbon were found to be 0.286 for red oak(1), 0.047 for balsam(1), 0.020 for yellow poplar(2), and 0.116 for mockernut hickory(2). 1-Eicosanol emission rates from wood smoke were calculated as 0.3 ug/g, 0.1 ug/g, and 1.0 ug/g from oak, eucalyptus and pine, respectively(3). 1-Docosanol emission rate from road dust samples was 2.1 ug/g(4).

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-eicosanol can be estimated to be 4.4X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-eicosanol is expected to be immobile in soil.

Natural Pollution Sources · 1 件

1-Eicosanol has been found in wood smoke from red oak(1), balsam(1), yellow poplar(2), mockernut hickory(2), eucalyptus(3) and pine(3). 1-Eicosanol emission rates from green leaf composite samples and dead leaves were 34 ug/g and 17 ug/g, respectively(4).

Atmospheric Concentrations · 2 件

URBAN/SUBURBAN: 1-Eicosanol was found in California at atmospheric concentrations of 2.0 ng/cu m, and 2.1 ng/cu m in Bakersfield and Fresno, respectively(1).

RURAL/REMOTE: 1-Eicosanol was found in California at an atmospheric concentration of 0.2 ng/cu m in Kern Wildlife Refuge(1). 1-Eicosanol was measured in the Agrafa Mountains, Greece at 0.23-0.39 ng/cu m from July 27 to August 9, 1998(2).

Fish/Seafood Concentrations · 1 件

1-Eicosanol was detected in lake trout caught at Apostle Island, WI in Lake Superior on Sept 15, 1977 and at Rockport, MI in Lake Huron on Nov 19, 1977. 1-Eicosanol was also found in Walleye caught at Anchor Bay, Mi in Lake St. Clair on Nov 17, 1977 and Dunkirk, PA in Lake Erie on Oct 21, 1977(1).

Artificial Pollution Sources1-Eicosanol's production and use in lubricants, rubber, plastics and textiles(1) may result in its release to the environment through various waste streams(SRC). 1-Eicosanol has been identified in paved road dust and cigarette smoke(2).
Environmental BiodegradationAEROBIC: While experimental data on 1-eicosanol where not available(SRC, 2006), calculations done on the chemical structure indicate that 1-eicosanol should biodegrade rapidly(1).
Sediment/Soil ConcentrationsSEDIMENT: 1-Eicosanol was reported as extractable concentrations of 73-84 ng/g and bonded concentrations of 53 to 74 ng/g in anoxic continental slope sediment off southwestern Taiwan(1).
Environmental Bioconcentration · 1 件

An estimated BCF of 10 was calculated for 1-eicosanol(SRC), using an estimated log Kow of 8.7(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).

安全データ

wgk
-
tsca
TSCA listed
hs_code
2905 19 00
化審法
(2)-217
safety_code
22-24/25
自然発火温度
245 °C
ストレージクラス
11 - Combustible Solids
有毒物質データの
629-96-9(Hazardous Substances Data)

2023: 550,000 - <700,000 lb

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).

(1986) >1 million-10 million pounds

(1990) >1 million-10 million pounds

(1994) >1 million-10 million pounds

For more U.S. Production (Complete) data for 1-EICOSANOL (6 total), please visit the HSDB record page.

Consumer UsesCleaning agent
Industry UsesSurfactant (surface active agent)
Methods of ManufacturingZiegler synthesis (trialkylaluminum process).
Formulations/Preparations · 3 件

Grade:Technical, 99%.

Trade names: ALFOL 20+ Alcohol; Cachalot Arachidyl Alcohol AR-20; Nacol 20-95; NACOL 20-95

Trade name mixtures: Covacrem LP; Covacrem MK; Macamat Wax; Micromac Wax; Montanov 202

Household ProductsInformation on 9 consumer products that contain Arachidyl alcohol in the following categories is provided:
Use Classification · 3 件

EPA Safer Chemical Functional Use Classes -> Emollients

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

Cosmetics -> Emollient

General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing

1-Eicosanol: ACTIVE

応用分野 · 3 件

用途トリートメント / コンディショナー,化粧水 / 乳液 / クリーム,ファンデーション / 下地,アウトバスヘアケア

使用1-Eicosanol has been used:in gradient HPLC-charged aerosol detection method for the detection of different lipidsas internal standard during determination of policosanol′s high molecular weight alcohols (policosanol′s fatty alcohols) in fish oil by GC

一般的な説明The polymorphism of 1-eicosanol has been studied by X-ray powder diffraction, differential scanning calorimetry (DSC), Raman scattering and IR spectroscopy.

調製方法

純化方法Crystallise the C20 alcohol from *benzene or *benzene/pet ether. [Beilstein 1 IV 1900.]

補足説明

定義本品は、次の化学式で表される脂肪族アルコールである。

定義ChEBI: A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of 20 carbon atoms.