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Itaconic acid

Itaconic acid structure

CAS No:
97-65-4
Formula:
C5H6O4
Chemical Name:
Itaconic acid
Synonyms:
Butanedioic acid,2-methylene-;Succinic acid,methylene-;Butanedioic acid,methylene-;2-Methylenebutanedioic acid;Itaconic acid;Methylenesuccinic acid;2-Propene-1,2-dicarboxylic acid;Propylenedicarboxylic acid;Methylenebutanedioic acid;2-Methylenesuccinic acid;NSC 3357;4-Hydroxy-2-methylene-4-oxobutanoic acid;2-Methylidenebutanedioic acid;1887074-72-7
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

white to light beige crystalline powder

DryPowder; Liquid; OtherSolid; PelletsLargeCrystals|Solid

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 acid, an olefinic compound and a lipid. It derives from a succinic acid. It is a conjugate acid of an itaconate(2-).

Itaconic acid Basic Attributes

Molecular Weight：

130.1

Exact Mass：

130.10

BRN：

1759501

EC Number：

202-599-6

UNII：

Q4516562YH

NSC Number：

3357

DSSTox ID：

DTXSID2026608

Color/Form：

RHOMBIC CRYSTALS FROM BENZENE|WHITE CRYSTALS

HScode：

29171990

Characteristics

PSA：

74.6

XLogP3：

-0.1

Appearance：

White to light beige Crystalline Powder or Crystals

Density：

1.632 g/cm³

Melting Point：

162-164 °C (decomp)

Boiling Point：

108 °C

Flash Point：

268°C

Water Solubility：

soluble in water, acetone, methanol, hexane and ethanol. Slightly soluble in benzene, chloroform, carbon disulfide and petroleum ether.

Storage Conditions：

Store below +30°C.

Vapor Pressure：

0.0000115 Pa (20 °C)

Toxicity：

LD50 orally in Rabbit: > 2000 mg/kg

Odor：

CHARACTERISTIC ODOR

Dissociation Constants：

ACID DISSOCIATION CONSTANTS: 3.84 & 5.55

Collision Cross Section：

131.7 Å² [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|118.7 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|119.1 Å² [M-H]-

Experimental Properties：

HYGROSCOPIC

Safety Information

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P273, P280, P305+P351+P338, P310, P501

Hazard Statements：

H318

GHS Classification：

|Danger|H315 (15.69%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 543 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310

Drug Information

Human Toxicity Excerpts：

IT IS PROBABLY MILD IRRITANT.

MeSH Entry Terms：

itaconate

Itaconic acid Use and Manufacturing

Methods of Manufacturing

1. The fermentation method is prepared by the biochemical action of Aspergillus terreus with carbohydrates (glucose, starch, etc.) plus appropriate amounts of nitrogen sources and inorganic salts. 2. According to different sources of raw materials, chemical synthesis methods can be divided into the following two types: (1) Agricultural products are used as raw materials. Such raw materials include citric acid, isocitric acid, aconitic acid or their anhydrides. Using citric acid as a raw material and supported phosphate as a catalyst, the reaction is carried out at 290-340°C to obtain citraconic acid, which is then heated to 220°C for isomerization to obtain itaconic acid. (2) Using petrochemical products as raw materials, using succinic anhydride or succinic acid diesters as raw materials, using thorium salt as a catalyst, and reacting with formaldehyde to generate citraconic acid, which is then heated for isomerization to obtain itaconic acid. 3. The new chemical synthesis method uses maleic anhydride as the main raw material to synthesize itaconic acid through a four-step reaction of esterification, addition, methyleneization and hydrolysis.

Uses

It is an important monomer for the preparation of synthetic fibers, synthetic resins and plastics, and ion exchange resins; it can also be used as a mounting agent for carpets, a coating agent for paper, a binder, and a dispersion latex for coatings. The ester derivatives of itaconic acid can be used for copolymerization of styrene and the like or plasticizers of polyvinyl chloride.

Adhesives and sealant chemicals

Adhesives and sealants

Production

1,000,000 - 10,000,000 lb

Manufacturing Info：

Adhesive manufacturing|Butanedioic acid, 2-methylene-: ACTIVE

Use Classification：

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]

Computed Properties

Molecular Weight:130.10
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:130.02660867
Monoisotopic Mass:130.02660867
Topological Polar Surface Area:74.6
Heavy Atom Count:9
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Succinic anhydride

Maleic anhydride

Formaldehyde

Glucose

Citric acid

Starch

Downstream Products

Methacrylic acid

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Guide of Itaconic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
Downstream Products
Recommended Suppliers
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Itaconic acid

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