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1-에이코사놀

1-Eicosanol

HCID 12404
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
28679-05-2
표준 SMILES
CCCCCCCCCCCCCCCCCCCCO
InChIKey
BTFJIXJJCSYFAL-UHFFFAOYSA-N
분자식
C20H42O
평균 분자량
298.5 g/mol
단동위원소 질량
298.32356596

개요

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.

이름 및 식별자

우선 이름
1-Eicosanol
IUPAC
icosan-1-ol
현지명
1-에이코사놀
영어명
1-Eicosanol
분자식
C20H42O
분자량
298.55

이름 및 동의어

1-EICOSANOLIcosan-1-ol629-96-9Arachidyl alcoholArachidic alcoholArachic alcoholEicosyl alcoholN-Eicosanol1-IcosanolN-1-EicosanolPri-N-eicosyl alcoholNSC 120887
이름 더 보기
1-에이코사놀아라키딜알코올1-아이코사놀EICOSANOLEICOSAN-1-OLIcosyl AlcoholARACHYL ALCOHOLIcosanolARACHIDYL
HSDB 57311QR1QRA9BUEINECS 211-119-4AI3-36485NSC-1208871-EICOSANOL [HSDB]DTXSID0027272CHEBI:75627

데이터베이스 식별자

CAS
28679-05-2、629-96-9
PubChem CID
12404
DTXSID
DTXSID0027272
ChEMBL
CHEMBL451717
ChEBI
CHEBI:75627
UNII
1QR1QRA9BU
EC Number
211-119-4
Nikkaji
J11.549E

물성

구조 계산 물성

XLogP
9.5
극성 표면적
20.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
18
무거운 원자 수
21
형식 전하
0
복잡도
167

실험 및 물리화학적 성질

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

White, wax-like solid

WAX FROM ALC AND CRYSTALS FROM CHLOROFORM

Solubility · 2건

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 · 2건

66.1 °C

66.1 °C

Vapor Pressure0.00000004 [mmHg]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 4건

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 · 1건

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/

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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

용도 및 제조

Uses · 4건

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 · 6건

관련 반응

7건
반응 기록 만들기
HRID 97957 반응식
HRID 97957반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 135937 반응식
HRID 135937반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 247719 반응식
HRID 247719반응물로uspto-grants-1987_11
HRID 414169 반응식
HRID 414169반응물로uspto-grants-1988_12
HRID 583018 반응식
HRID 583018반응물로uspto-grants-1999_07
HRID 814789 반응식
HRID 814789반응물로Test data from https://doi.org/10.1039/C8SC04228D
HRID 1377380 반응식
HRID 1377380반응물로uspto-grants-1997_09

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Refractive Index
Index of refraction = 1.450 at 20 °C/D

물리화학적 성질

녹는점
62 · 62-65 °C(lit.)
끓는 점
220 · 220-225°C 3mm
밀도
0 · 0,841 g/cm3
증기 밀도
7.4 · 7.4 (vs air)
증기압
0.1 mm · <0.1 mm Hg ( 20 °C)
굴절률
1.435 · 1.4350
인화점
195 °C · 195°C
저장 조건
30 °C · Store below +30°C.
용해도
23 °C에서 · 물: 23°C에서 약간 용해됨0.001g/L
산도 계수 (pKa)
15.2 · 15.20±0.10(Predicted)
물리적 상태
펠릿, 분말 또는 덩어리
색상
하얀색
수용성
물에 불용성.
BRN
1705104 · 1705104
Henry's Law Constant
4.7 · 4.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
화장품 원료 기능
유화 안정화점도 조절피부 컨디셔닝 - 보습제
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
NIST
1 · 1-Eicosanol(629-96-9)
EPA
1 · 1-Eicosanol (629-96-9)

화학적 성질

white fluffy crystalline powder

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

Interactions · 3건

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 · 3건

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 · 1건

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 · 1건

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 · 1건

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 · 2건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
-
tsca
TSCA listed
HS 번호
2905 19 00
safety_code
22-24/25
기존화학 물질
KE-13066
자연 발화 온도
245 °C
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
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 · 3건

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 · 3건

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 · 2건

All Other Basic Organic Chemical Manufacturing

1-Eicosanol: ACTIVE

응용 분야 · 2건

용도1-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

일반 설명The polymorphism of 1-eicosanol has been studied by X-ray powder diffraction, differential scanning calorimetry (DSC), Raman scattering and IR spectroscopy.

추가 설명

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