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Dibutyl Sebacate

HCID 7986
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
109-43-3
標準SMILES
CCCCOC(=O)CCCCCCCCC(=O)OCCCC
InChIKey
PYGXAGIECVVIOZ-UHFFFAOYSA-N
分子式
C18H34O4
平均分子量
314.5 g/mol
単同位体質量
314.24570956

概要

Dibutyl decanedioate is a fatty acid ester.

名称と識別子

優先名称
Dibutyl Sebacate
IUPAC
dibutyl decanedioate
英語名
Dibutyl sebacate
分子式
C18H34O4
分子量
0

名称と別名

DIBUTYL SEBACATEDibutyl decanedioate109-43-3Butyl sebacateDi-n-butyl sebacateDecanedioic acid, dibutyl esterKodaflex DBSStaflex DBSDibutyl sebacinateMonoplex DBSBis(n-butyl) sebacateSebacic acid, dibutyl ester
名称をさらに表示
1,10-dibutyl decanedioateDi-n-butylsebacateBis(n-butyl)sebacaten-Butyl sebacateFEMA No. 2373Dibutyl 1,8-octanedicarboxylateDibutylester kyseliny sebakovePX 404

データベース識別子

CAS
109-43-3
PubChem CID
7986
DTXSID
DTXSID1041847
ChEMBL
CHEMBL2106225
ChEBI
CHEBI:165632
UNII
4W5IH7FLNY
EC Number
203-672-5
Nikkaji
J1.968B

物性

構造計算による物性

XLogP
5.3
極性表面積
52.6 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
17
重原子数
22
形式電荷
0
複雑度
248

実験および物理化学的性質

Chemical ClassesOther Classes -> Esters, Other
Polymers · 2 件

Plastics -> PUR; PVC (soft)

Plastics -> Plasticisers

Cosmetics · 2 件

Cosmetic ingredients (Dibutyl Sebacate) -> CIR (Cosmetic Ingredient Review)

Skin conditioning; Hair conditioning; Plasticiser; Film forming; Emollient

OdorOdorless
PlasticizersPlasticizer
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 件

0.9405 @ 15 °C

Relative density (water = 1): 0.9

0.936-0.940 (20 °C)

Flavoring AgentsEU Flavoring substances
Color/FormColorless liquid
Solubility · 6 件

Soluble in ethyl ether

water solubility = 40 mg/l @ 20 °C

0.04 mg/mL at 20 °C

Solubility in water: none

insoluble in water; soluble in alcohol; miscible in oil

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 82.8% (410 of 495) of all reports.

Warning

H315 (16.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 495 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Decanedioic acid, dibutyl ester

Decanedioic acid, 1,10-dibutyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Decanedioic acid, 1,10-dibutyl ester 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: Dibutyl sebacate (EC: 203-672-5)

Decanedioic acid, dibutyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Fire HazardsCombustible.
Hazards Summary · 1 件

Safe when used as a flavoring agent in food; [JECFA] Causes somnolence, diarrhea, and abnormal liver function tests in lethal-dose feeding studies of rats; [RTECS] May cause skin sensitization; [ICSC] Emergency treatment: Irritants; Considered to be practically non-toxic by oral and dermal exposure; [HSDB] Search by CAS# found no article relating to allergic dermatitis; [PubMed] A skin irritant; No sensitizing effects known; [MSDSonline]

化学と産業

薬理情報

Metabolism/MetabolitesIN VITRO PANCREATIC LIPASE HYDROLYZES DIBUTYL SEBACATE AS RAPIDLY AS IT DOES TRIOLEIN, & FROM THIS IT CAN BE CONCLUDED THAT THE PLASTICIZER IS METABOLIZED IN THE BODY BY SAME ROUTE AS FATS.
Cellular LocationsExtracellular

用途と製造

Uses · 5 件

CIR ingredient: Dibutyl Sebacate

Used as plasticizer, rubber softener, dielectric liquid, flavoring ingredient, and additive to cosmetics and perfumes; [HSDB]

SYNTHETIC FLAVORING ADJUVANT

Plasticizer, rubber softener, dielectric liquid, cosmetic and perfumes, flavoring ingredient

Plastics -> Typical concentration range in plastic materials -> 10.0 - 35.0%

U.S. Production · 3 件

2023: 550,000 - <700,000 lb

(1972) 2.04X10+9 GRAMS

(1975) 2.54X10+9 G (INCL 2-ETHYLHEXYL)

Consumer UsesPigment
Industry UsesPigment
Methods of ManufacturingBY DISTILLATION OF SEBACIC ACID WITH BUTYL ALCOHOL IN PRESENCE OF CONCN HCL IN BENZENE SOLN OR BY REACTING BUTYL ALCOHOL & SEBACYL CHLORIDE...
Use Classification · 6 件

EPA Safer Chemical Functional Use Classes -> Emollients;Skin Conditioning Agents;Solvents

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

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information

関連反応

2 件
反応記録を作成
HRID 1504581 の反応式
HRID 1504581生成物としてuspto-grants-2015_12
HRID 1650784 の反応式
HRID 1650784反応物としてuspto-grants-1990_05

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

(in ethanol)

Flash Point · 2 件

353 °F (178 °C) (OPEN CUP)

167 °C

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
FDA Requirements · 3 件

Dibutyl sebacate 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 2) 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.

Dibutyl sebacate is an indirect food additive for use only as a component of adhesives.

Prior-Sanctioned Food Ingredients: Substances classified as plasticizers, when migrating from food-packaging material shall include: dibutyl sebacate.

EPA Safer ChemicalChemical: Dibutyl sebacate
NFPA Hazard Classification · 3 件

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesSkin Irrit. 2 (16.8%)
Hazardous Reactivities and IncompatibilitiesCombustible liquid when exposed to heat or flame; can react with oxidizing materials.

安全と保護具

Fire FightingUse water spray, powder, carbon dioxide.
First Aid Measures · 4 件

Fresh air, rest.

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

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Rest.

Safe StorageWell closed.
Fire Fighting Procedures...CARBON DIOXIDE, DRY CHEM.
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 件

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskA harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionSTRICT HYGIENE!
Ingestion PreventionDo not eat, drink, or smoke during work.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from a water solubility of 40 mg/l(2) and a regression-derived equation(3), indicates that dibutyl sebacate is expected to have low mobility in soil(SRC). Volatilization of dibutyl sebacate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.7X10-6 mm Hg(4) and water solubility of 40 mg/l(2). Dibutyl sebacate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Dibutyl sebacate and other plasticizers were readily biodegraded by pure bacterial and fungal cultures(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from a water solubility of 40 mg/l(2) and a regression-derived equation(3), indicates that dibutyl sebacate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 4.8X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.7X10-6 mm Hg(4) and water solubility of 40 mg/l(2). A base-catalyzed second-order hydrolysis rate constant of 0.05 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 4.5 years and 166 days at pH values of 7 and 8, respectively(5). Dibutyl sebacate and other plasticizers were readily biodegraded by pure bacterial and fungal cultures(6,7). According to a classification scheme(8),an estimated BCF of 77(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl sebacate, which has a vapor pressure of 4.7X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dibutyl sebacate 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 estimated rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase dibutyl sebacate may be removed from the air by wet and dry deposition(SRC). Dibutyl sebacate may also undergo direct photolysis in the environment since this compound contains functional groups that can absorb light greater than 290 nm(4).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1 件

The Koc of dibutyl sebacate is estimated as 575(SRC), using a water solubility of 40 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibutyl sebacate is expected to have low mobility in soil(SRC).

Natural Pollution SourcesNOT REPORTED FOUND IN NATURE.
Artificial Pollution SourcesDibutyl sebacate's production and use as a plasticizer, rubber softener, flavoring agent and cosmetic and perfume ingredient(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

Dibutyl sebacate was degraded by pure bacterial and fungal cultures over 1 to 4 week incubation periods in shake flask experiments(1). Pure strains of the fungus Fusarium were shown to degrade dibutyl sebacate and several other plasticizers(2).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 件

An estimated BCF of 77 was calculated for dibutyl sebacate(SRC), using a water solubility of 40 mg/l(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).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for dibutyl sebacate is estimated as 4.8X10-8 atm-cu m/mole(SRC) from its vapor pressure, 4.7X10-6 mm Hg(1), and water solubility, 40 mg/l(2). This Henry's Law constant indicates that dibutyl sebacate is expected to be essentially nonvolatile from water surfaces(3). Dibutyl sebacate's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is not expected to be an important environmental fate process(SRC). Volatilization from dry soil surfaces is not expected to be an important fate process(SRC) based on the vapor pressure of this compound(1).

Non-Human Toxicity Excerpts · 3 件

...In a 2 yr period study, dietary levels of 0.25, 1.25, and 6.25% dibutyl sebacate were fed to rats. The data showed no weight, hematologic, or bone marrow changes, but some isolated inflammatory changes in the lungs, some nephrosis and fatty livers at the highest dose.

Toxicologic data indicate that the material is practically nontoxic orally or by dermal contact.

ORAL /ACUTE/ TOXICITY. DOSES OF 1-32 G/KG BODY WT WERE ADMIN TO YOUNG RATS 5-10 WK OLD & WEIGHING 60-75 G. ALL DOSES UP TO 16 G/KG WERE TOLERATED... DOSES OF 4-8 G/KG BODY WT WERE ADMIN TO RATS IM WITHOUT PRODUCING ANY OBSERVABLE REACTIONS.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of dibutyl sebacate with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 21 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.05 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4.5 years and 166 days at pH values of 7 and 8, respectively(2). The expected hydrolysis products are butanol and sebacic acid. Dibutyl sebacate may also undergo direct photolysis in the environment since this compound contain a functional group that can absorb light greater than 290 nm(3).

法規制情報

FDA Requirements · 3 件

Dibutyl sebacate 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 2) 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.

Dibutyl sebacate is an indirect food additive for use only as a component of adhesives.

Prior-Sanctioned Food Ingredients: Substances classified as plasticizers, when migrating from food-packaging material shall include: dibutyl sebacate.

· 6 件

Transportation Equipment Manufacturing

Decanedioic acid, 1,10-dibutyl ester: ACTIVE

REPORTED USES: NON-ALCOHOLIC BEVERAGES 1.0-5.0; ICE CREAM, ICES, ETC 2.0-5.0 PPM; CANDY 15 PPM; BAKED GOODS 15 PPM.

DIBUTYL SEBACATE IS A VERY GOOD PLASTICIZER FOR POLYVINYL CHLORIDE, TO WHICH IT IMPARTS EXCELLENT LOW-TEMPERATURE RESISTANCE, FLEXIBILITY BEING RETAINED OVER WIDE TEMP RANGE.

IT IS...PLASTICIZER OF CHOICE FOR CELLULOSE ACETOBUTYRATE, POLYVINYL BUTYRAL, RUBBER HYDROCHLORIDE, & POLYVINYLIDENE CHLORIDE. IT IS EQUALLY COMPATIBLE WITH NITROCELLULOSE, ETHYL CELLULOSE, POLYSTYRENE, & MANY SYNTHETIC RUBBERS.

...ITS USE IN FOOD-PACKAGING INDUSTRY IS AUTHORIZED IN FRANCE, US, & ITALY.

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