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283258

Sigma-Aldrich

Sebacic acid

99%

Synonym(s):

Decanedioic acid

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About This Item

Linear Formula:
HO2C(CH2)8CO2H
CAS Number:
Molecular Weight:
202.25
Beilstein:
1210591
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

1 mmHg ( 183 °C)

Assay

99%

bp

294.5 °C/100 mmHg (lit.)

mp

133-137 °C (lit.)

solubility

ethanol: 100 mg/mL
ketones and ethers: soluble

functional group

carboxylic acid

SMILES string

OC(=O)CCCCCCCCC(O)=O

InChI

1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)

InChI key

CXMXRPHRNRROMY-UHFFFAOYSA-N

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General description

Sebacic acid is a castor oil-derived dicarboxylic acid. It is widely used to produce polymers, plasticizers, lubricants, and corrosion retardants. It can act as a pH corrector in the cosmetic products formulations. Sebacic acid is also used as a precursor to prepare sebacate esters such as diisopropyl sebacate, diethylhexyl sebacate, and dibutyl sebacate.

Application

Sebacic acid has been used in the synthesis of:
  • biodegradable and elastomeric polyesters [poly(glycerol sebacate)]
  • novel bio-nylon, PA5.10
  • novel temperature-response hydrogel based on poly(ether-ester anhydride) nanoparticle for drug-delivery applications

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The plasticizer market: an assessment of traditional plasticizers and research trends to meet new challenges
Rahman M and Brazel CS
Progress in Polymer Science, 29, 1223-1248 (2004)
Augmented bio-based lipids for cosmetics
Duprat-de-Paule, et al.
Oilseeds and fats, Crops and Lipids, 25, D503-D503 (2018)
Biodeterioration of synthetic materials-A brief review
Flemming H-C, et al.
Materials and Corrosion, 61, 986-992 (2010)
Stefanie Kind et al.
Metabolic engineering, 25, 113-123 (2014-05-17)
Polyamides are important industrial polymers. Currently, they are produced exclusively from petrochemical monomers. Herein, we report the production of a novel bio-nylon, PA5.10 through an integration of biological and chemical approaches. First, systems metabolic engineering of Corynebacterium glutamicum was used
Min Ji Kim et al.
BioMed research international, 2014, 956952-956952 (2014-06-24)
We synthesized and evaluated biodegradable and elastomeric polyesters (poly(glycerol sebacate) (PGS)) using polycondensation between glycerol and sebacic acid to form a cross-linked network structure without using exogenous catalysts. Synthesized materials possess good mechanical properties, elasticity, and surface erosion biodegradation behavior.

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