Suberic acid
[CAS# 505-48-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: Suberic acid
• Synonyms: Octanedioic acid
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.20
• CAS Registry Number: 505-48-6
• EC Number: 208-010-9
• SMILES: C(CCCC(=O)O)CCC(=O)O

Properties

• Melting point: 141-144 ºC
• Boiling point: 230 ºC (15 mmHg)
• Flash point: 203 ºC
• Water solubility: 0.6 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H319
• Precautionary Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Suberic acid, also known as octanedioic acid, was first discovered in the early 19th century. It is a naturally occurring dicarboxylic acid found in certain plant and animal sources, as well as in petroleum derivatives. The name "suberic" is derived from the Latin word "suber," meaning cork, as it was initially isolated from cork oak. The compound's chemical structure consists of an eight-carbon chain with two carboxylic acid groups (-COOH) at either end. Suberic acid can be synthesized through various methods, including oxidation of suberic aldehyde or ester hydrolysis.

Suberic acid and its derivatives are used in pharmaceutical formulations for drug delivery and as excipients. They can act as solubilizers, stabilizers, and pH modifiers in pharmaceutical preparations. Additionally, suberic acid esters are investigated for their potential as prodrugs, where they can be enzymatically cleaved to release active pharmaceutical ingredients in a controlled manner.

Suberic acid derivatives are utilized in cosmetics and personal care products for their emollient and moisturizing properties. They are incorporated into creams, lotions, and skincare formulations to improve skin hydration and texture. Suberic acid esters also function as emulsifiers and surfactants in cosmetic formulations, enhancing product stability and texture.

Suberic acid is a building block for the synthesis of various polymers and resins. Its bifunctional nature allows it to undergo polymerization reactions, forming linear or cross-linked polymer chains. Suberic acid-based polymers are used in coatings, adhesives, and sealants.

Suberic acid derivatives are employed in agriculture as surfactants and wetting agents in pesticide formulations. They help improve the spread and adherence of pesticides on plant surfaces, enhancing their effectiveness in pest control. Additionally, suberic acid-based compounds can serve as chelating agents in agricultural fertilizers, facilitating the uptake of essential nutrients by plants.

Suberic acid is used in the textile industry as a mordant in dyeing processes. It helps fix dyes onto fabrics, improving colorfastness and wash resistance. Suberic acid-based mordants are particularly effective for natural fibers such as cotton and wool.

Suberic acid and its derivatives are valuable tools in chemical research and organic synthesis. They serve as intermediates for the synthesis of more complex organic compounds and can be modified to introduce specific functional groups.

References

2023. 1,12-Dodecanediol-Based Polyesters Derived from Aliphatic Diacids with Even Carbons: Synthesis and Characterization. Journal of Polymers and the Environment, 31(6).
DOI: 10.1007/s10924-023-02884-0

2022. Activation of OR10A3 by Suberic Acid Promotes Collagen Synthesis in UVB-Irradiated Dermal Fibroblasts via the cAMP-Akt Pathway. Cells, 11(24).
DOI: 10.3390/cells11243961

1949. A CONVENIENT PREPARATION OF SUBERIC ACID. CONCERNING THE HOMOGENEITY AND USE IN SYNTHESIS OF POLYMETHYLENE CHLOROBROMIDE PREPARATIONS. The Journal of Organic Chemistry, 14(1).
DOI: 10.1021/jo01153a007