基本情報
- 標準SMILES
C=C(CC(=O)O)C(=O)O- InChIKey
LVHBHZANLOWSRM-UHFFFAOYSA-N- 分子式
- C5H6O4
- 平均分子量
- 130.1 g/mol
- 単同位体質量
- 130.02660867
概要
Itaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. It has a role as a fungal metabolite and a human metabolite. It is a dicarboxylic fatty acid, a dicarboxylic acid and an olefinic compound. It is functionally related to a succinic acid. It is a conjugate acid of an itaconate(2-).
名称と識別子
- 優先名称
- Itaconic acid
- IUPAC
- 2-methylidenebutanedioic acid
- 英語名
- Poly(itaconic acid)
- 分子式
- C15H18O12X2
- 分子量
- 130.1
名称と別名
Itaconic acid97-65-42-Methylenesuccinic acid2-methylidenebutanedioic acidMETHYLENESUCCINIC ACIDMethylenebutanedioic acidPropylenedicarboxylic aciditaconateButanedioic acid, methylene-2-Propene-1,2-dicarboxylic acidSuccinic acid, methylene-2-methylenebutanedioic acid
名称をさらに表示
Poly(itaconic acid)itaconicacidpolymersITACONIC ACID POLYMERitaconic acid homopolymerpoly(2-methylenesuccinicacid)methylenesuccinicacidpolymersmethylene-butanedioicacihomopolymer
DTXSID2026608NSC-3357Q4516562YHDTXCID006608CHEBI:30838methylidenebutanedioateRefChem:792464hydron;2-methylidenebutanedioate
データベース識別子
- CAS
25119-64-6、97-65-4- PubChem CID
- 811
- DTXSID
DTXSID2026608- ChEMBL
CHEMBL359159- ChEBI
CHEBI:30838- UNII
- Q4516562YH
- EC Number
- 202-599-6
- Nikkaji
- J38.149G
物性
構造計算による物性
- XLogP
- -0.1
- 極性表面積
- 74.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 3
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 158
実験および物理化学的性質
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
PolymersPlastics & Rubber -> Other Monomers
SpringerMaterials PropertiesCrystal structure
OdorCHARACTERISTIC ODOR
Density1.632
Color/Form
RHOMBIC CRYSTALS FROM BENZENE
WHITE CRYSTALS
Solubility
1 G DISSOLVES IN 12 ML WATER, 5 ML ALC; VERY SLIGHTLY SOL IN BENZENE, CHLOROFORM, CARBON DISULFIDE, PETROLEUM ETHER
SOL IN ACETONE
76.8 mg/mL at 20 °C
Boiling Point268 °C, SUBLIMES
Melting Point
162-164 °C WITH DECOMP, ALSO REPORTED AS 172 °C
175 °C
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
Liquid; Large Crystals; Dry Powder; Other Solid
Hygroscopic solid; [Merck Index] White crystalline powder; [MSDSonline]
Solid
Dissociation ConstantsACID DISSOCIATION CONSTANTS: 3.84 & 5.55
物理化学的性質
- 酸解離定数(Pka)
- 3.85 · 3.85 (pKa1)
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 5.9% (33 of 555) of reports.
Danger
H315 (14.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, 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 555 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
危険有害性情報
Regulatory Information
Chemical: Butanedioic acid, methylene-
Butanedioic acid, 2-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanedioic acid, 2-methylene- 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: 27-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14392
Methylenesuccinic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Butanedioic acid, methylene-: Environment tier I assessment
Hazards SummaryCorrosive to eyes; [eChemPortal: ERMA] Oral LD50 (rat) = 2969 mg/kg; NOEL = 500 mg/kg/d (highest dose tested) for oral repeated dose testing of rats for 4 weeks; [eChemPortal: SIDSUNEP] An irritant; [MSDSonline]
Hazard Classes and Categories
Skin Irrit. 2 (14.8%)
Serious eye damage/eye irritation - Category 1
毒性情報
Human Toxicity ExcerptsIT IS PROBABLY MILD IRRITANT.
Non-Human Toxicity Excerpts
...IT MAY INHIBIT UTILIZATION OF SUCCINIC ACID WHEN FED IN RELATIVELY LARGE DOSES TO RATS. 1% IN THE DIET OF RATS CAUSED SLOW GROWTH. A SINGLE LARGE ORAL DOSE CAUSES AN INCREASED OUTPUT OF SUCCINIC ACID IN RABBIT URINE.
ITACONIC ACID RETARDED GROWTH OF PEAS, INHIBITED CHLOROPHYLL DESTRUCTION & CHLOROPHYLLASE ACTIVITY IN RADISH LEAF DISKS, & HASTENED FLOWERING & RIPENING OF TOMATOES.
化学と産業
薬理情報
Cellular LocationsMitochondria
用途と製造
Uses
Used in copolymerization and to make resins, plasticizers, and lube oil additives; [HSDB] Used as a comonomer in the production of acrylic fibers and latex; [eChemPortal: SIDSUNEP]
COPOLYMERIZATIONS; RESINS; PLASTICIZERS; LUBE OIL ADDITIVES; INTERMEDIATE
U.S. Production2023: 2,500,000 - <4,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesSurface modifier
Methods of Manufacturing
OBTAINED BY DRY DISTILLATION OF CITRIC ACID AND SUBSEQUENT TREATMENT OF THE ANHYDRIDE WITH WATER. PRODUCED ON A LARGE SCALE BY SUBMERGED AEROBIC FERMENTATION USING ASPERGILLUS TERREUS AND LOW COST CARBOHYDRATES FROM BEET OR CANE: KANE ET AL, US PATENT 2,385,283 (1945 TO PFIZER).
SYNTHESIS FROM PROPARGYL CHLORIDE, CARBON MONOXIDE, NICKEL CARBONYL & WATER: CHIUSOLI, US PATENT 3,025,320 (1962 TO MONTECATINI).
Household ProductsInformation on 1 consumer products that contain Methylenesuccinic acid in the following categories is provided:
General Manufacturing Information
Petrochemical Manufacturing
Butanedioic acid, 2-methylene-: ACTIVE
サプライヤー2 社
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