UNDECANEDIOIC ACID

Undecanedioic Acid is a long-chain dicarboxylic acid with two reactive terminal groups.
Polyester, polyamide and specialty resin production commonly uses Undecanedioic Acid.
Undecanedioic Acid provides flexibility, durability and water resistance to selected polymer structures.

CAS Number: 1852-04-6
EC Number: 217-440-6
Molecular Formula: C₁₁H₂₀O₄
Molecular Weight: 216.27 g/mol
MDL Number: MFCD00004444

Synonyms: UDDA, UDA, DC11, 1,11-Undecanedioic acid, 1,9-Nonanedicarboxylic acid, Hendecanedioic acid, Nonamethylenedicarboxylic acid, Undecanedionic acid, Undecandioic acid, Undecane-1,11-dioic acid, 1,9-Nonanedicarboxylate, 1,11-Undecanedioate, Decane-1,10-dicarboxylic acid (incorrect synonym, use 1,9-Nonanedicarboxylic acid), NSC-400241, NSC 400241, BRN 1780537, MFCD00004444, ChEBI CHEBI:73713, DTXSID0044862, FDA UNII 7059GFK8NV, EINECS 217-440-6, CAS 1852-04-6, Novacid DC11, Corvay UDDA

Undecanedioic Acid has the molecular formula C₁₁H₂₀O₄ and a molar mass of approximately 216.28 g/mol.
The structure of Undecanedioic Acid contains two terminal carboxylic acid groups connected by a nine-carbon methylene chain.

Undecanedioic Acid belongs to the family of long-chain alpha,omega-dicarboxylic acids.
The two reactive ends of Undecanedioic Acid make the material a versatile building block for polymer synthesis.

Undecanedioic Acid normally appears as a white or off-white crystalline solid.
The relatively long hydrocarbon chain gives Undecanedioic Acid both hydrophobic and carboxylic characteristics.

Water dissolves only a limited amount of Undecanedioic Acid under ordinary conditions.
Alcohols and several other organic solvents can dissolve Undecanedioic Acid more effectively when heated.

Undecanedioic Acid melts at a temperature slightly above 110°C.
The low volatility of Undecanedioic Acid supports its use in high-temperature synthesis processes.

Polymer manufacturers use Undecanedioic Acid in the production of specialized polyesters.
The long flexible chain of Undecanedioic Acid can improve softness and flexibility in selected polyester structures.

Undecanedioic Acid can react with diamines to produce long-chain polyamides.
Polyamides containing Undecanedioic Acid may provide flexibility, toughness and reduced moisture absorption.

Coating resins can incorporate Undecanedioic Acid to modify flexibility and surface properties.
The hydrophobic chain of Undecanedioic Acid can contribute to improved water resistance in selected formulations.

Adhesive manufacturers may use Undecanedioic Acid as an intermediate for polyester and polyamide resins.
Resins prepared with Undecanedioic Acid can provide balanced adhesion, flexibility and durability.

Undecanedioic Acid can undergo esterification with monoalcohols or polyols.
Esters prepared from Undecanedioic Acid find potential use in lubricants, plasticizers and specialty fluids.

Lubricant formulations can employ derivatives of Undecanedioic Acid to improve film formation and thermal performance.
The two carboxylic groups of Undecanedioic Acid allow the preparation of multifunctional lubricant additives.

Plasticizer developers investigate Undecanedioic Acid esters for flexible polymer applications.
The long carbon chain of Undecanedioic Acid can support low-temperature flexibility in suitable ester derivatives.

Undecanedioic Acid can serve as an intermediate for corrosion-control additives.
Metal salts and functional derivatives prepared from Undecanedioic Acid may contribute to protective surface films.

Organic synthesis uses Undecanedioic Acid as a linear bifunctional building block.
The terminal groups of Undecanedioic Acid permit controlled reactions at both ends of the molecule.

Undecanedioic Acid can be converted into acid chlorides, esters, amides and salts.
These transformations allow Undecanedioic Acid to support the development of numerous specialty chemicals.

Chemical and biotechnological oxidation methods can produce Undecanedioic Acid from suitable C₁₁ raw materials.
Purification and crystallization provide Undecanedioic Acid with controlled color and chemical purity.

Reaction temperature, catalyst selection and raw-material ratio influence polymerization involving Undecanedioic Acid.
Careful moisture control supports consistent reactions when Undecanedioic Acid participates in condensation polymerization.

Acid value, melting range and water content represent important quality parameters for Undecanedioic Acid.
Chromatographic and spectroscopic methods can confirm the purity and identity of Undecanedioic Acid.

A white to off-white crystalline solid with 11 carbon atoms in its straight chain and carboxylic acid groups at both termini, undecanedioic acid belongs to the family of long-chain aliphatic dicarboxylic acids (defined as containing 10 or more chain carbons) — a class valued for high-value-added applications in special lubricants for aerospace and military use, special materials for petroleum pipelines, automotive materials, high-grade plasticisers, tyre wear-resistance agents, high-grade paint coatings, pharmaceuticals, pesticides, and specialty polymers. Undecanedioic acid is distinguished from its nearest commercial neighbours, sebacic acid (C10) and dodecanedioic acid (C12), by its odd number of chain carbons — a structural feature that produces even-odd and odd-odd polyamides with distinctive hydrogen bond density patterns, lower melting points, and unusual crystallisation behaviour including the solvent-dependent conformational dimorphism described by Shi et al.

Uses of Undecanedioic Acid:
Undecanedioic acid is used as the C11 odd-carbon dicarboxylic acid monomer for the synthesis of a series of novel even-odd nylons (Nylon 6,11; 8,11; 10,11; 12,11) and odd-odd nylons (Nylon 5,11; 7,11; 9,11; 11,11) by step-heating melt polycondensation with the corresponding even- or odd-numbered diamines; the resulting polyamides exhibit intrinsic viscosities of 0.70–0.87 dL/g, melting temperatures of 182–209°C, and glass transition temperatures of 22–45°C as measured by DMA, with properties intermediate between those of short-chain and long-chain polyamide systems; these novel even-odd and odd-odd nylons are of interest for engineering plastic applications in automotive, electronic, and aerospace components where the unique combination of low moisture uptake, chemical resistance, and processing flexibility of odd-carbon-derived polyamides is required.
Undecanedioic acid is used for the production of synthetic ester-based lubricants by esterification with monohydric or polyhydric alcohols; the resulting diesters and polyol esters combine excellent viscosity index, low volatility, wide operating temperature range, and good thermal and hydrolytic stability, making them suitable for automotive engine oils, industrial gear oils, compressor oils, aerospace turbine lubricants, and low-temperature greases; undecanedioic acid-derived esters improve lubricant performance in high-temperature and extreme-pressure environments and increase the proportion of bio-based or renewable components in the lubricant product.
Undecanedioic acid is used as a corrosion inhibitor in water treatment formulations (closed-loop cooling water, cooling towers, boiler water), engine coolant and antifreeze compositions, metalworking fluids (cutting oils, rolling lubricants, grinding fluids), oil-and-gas processing fluids, and aqueous hydraulic fluids; it forms a thin, adherent protective film on metal surfaces (steel, copper, aluminium, cast iron) through carboxylate group adsorption, displacing water and corrosive ions from the metal surface and impeding oxidative attack; it can be formulated as the free acid or as its mono- or di-ammonium, sodium, or amine salt for improved water solubility in aqueous formulation systems.
Undecanedioic acid is used in the preparation of high-solid-content, low-VOC coatings and structural adhesives as a difunctional building block for polyester and polyamide binder resins, providing improved adhesion, weather resistance, and corrosion protection for metal, plastic, and composite substrates; in powder coating polyester resin formulations where the C11 chain segment contributes flexibility, impact resistance, and outdoor durability; and as a crosslinking agent or curing component in hot-melt adhesives and sealants where it improves adhesion strength and chemical resistance through crosslink network formation with polyamine, polyol, or epoxy resin co-reactants.
Undecanedioic acid is used as a pharmaceutical and specialty chemical intermediate for the synthesis of complex drug molecules — including proteolysis-targeting chimeras (PROTACs) with anticancer activity in mutant EGFR-expressing cancer cells (reported at 1 mM concentration), antifungal agents (active against Trichophyton rubrum, T. mentagrophytes, and Microsporum canis at 1 mM), and other bioactive compounds; as a synthetic intermediate for fragrances and aroma chemicals; in agrochemical synthesis; and as a building block for specialty surfactants and surface-active agents.
Undecanedioic acid and its derivatives are used in personal care products — shampoos, conditioners, skin creams, and cosmetics — as emollient, moisturiser, and conditioning agent, where the long hydrophobic C11 backbone combined with the two terminal carboxylic acid groups provides surface-active, film-forming, and skin-substantive properties; it is also classified by EPA as a binder, wetting agent (non-aqueous), lubricating agent, and plasticiser.

Benefits and Advantages of Undecanedioic Acid:
The odd-carbon C11 chain of undecanedioic acid — produced by an 11-carbon backbone between the two terminal carboxylic acid groups — enables the synthesis of a family of even-odd and odd-odd polyamides not accessible from even-chain diacids; these odd-chain-derived polyamides exhibit a distinctive reduction in inter-chain hydrogen bond density relative to their even-chain analogues, yielding lower melting temperatures, lower moisture absorption, better chemical resistance, and a broader processing window — properties of increasing interest in precision engineering applications and in bio-based polyamide development.
Undecanedioic acid is produced commercially by bio-fermentation routes (ω-oxidation of long-chain alkanes or microbial fermentation of fatty acids by Candida spp.), providing a renewable, bio-based origin consistent with green chemistry principles and sustainability requirements; like dodecanedioic acid, its bio-based supply pathway reduces dependence on petroleum-derived feedstocks and enables access to bio-based long-chain diacid monomers for sustainable polymer, lubricant, and specialty chemical production; the compound is REACH registered.
Undecanedioic acid's dual acid functionality at both chain termini combined with the C11 hydrophobic backbone gives it broad utility as a building block across esterification (lubricant esters, plasticiser esters, polyester resin synthesis), amidation (polyamide synthesis, corrosion inhibitor salt formation), and crosslinking (adhesive and sealant cure chemistry) reaction pathways from a single raw material; this multifunctional reactivity from a single long-chain bio-based molecule is a defining commercial advantage of the long-chain dicarboxylic acid family.
Undecanedioic acid exhibits unusual solvent-dependent conformational dimorphism characterised in detail by Shi et al.: solvents with high hydrogen-bond-donating (HBD) ability preferentially nucleate Form II, while solvents with no HBD ability yield Form I; this solvent-controlled polymorph selectivity is useful for targeted production of specific crystal forms with defined melting points, dissolution rates, and particle morphologies for pharmaceutical and fine chemical applications.

Features of Undecanedioic Acid:
Undecanedioic acid is a white to off-white crystalline solid at room temperature, available as powder or flakes; melting point 108–110°C (lit.); boiling point 389.33°C (rough estimate); density 1.1629 g/cm³ (rough estimate); vapour pressure 10 Pa at 20°C; pKa 4.48±0.10 (predicted); LogP 2.8 (at 25°C); water solubility 5.10 g/L at 21°C (slightly soluble, pH-dependent); soluble in methanol (10 mg/mL, clear), DMSO (20 mg/mL), ethanol (20 mg/mL), DMF (16 mg/mL), and diethyl ether; SMILES OC(=O)CCCCCCCCCC(O)=O; InChIKey LWBHHRRTOZQPDM-UHFFFAOYSA-N; refractive index 1.4421 (estimate); ΔfusH 39.65–41.20 kJ/mol (at 380–385 K); ΔsubH 141.5–158.6 kJ/mol.
Commercial specification (typical): appearance — white powder or flakes; undecanedioic acid content ≥98%; total acid ≥99%; moisture ≤0.6%; iron ≤10 ppm; melting point 110–114°C.
Undecanedioic acid exhibits solvent-dependent conformational dimorphism (Form I and Form II) with strong correlation between solute-solvent hydrogen-bond interactions and polymorph nucleation outcome, as characterised by Shi et al. using solution FTIR spectroscopy, quantitative powder X-ray diffraction, solid-state NMR, and quantum chemistry calculations; the difficulty of desolvation (linked to solute-solvent HBD interactions) markedly affects the degree of conformation rearrangement and the nucleation outcome; this polymorphism is relevant to controlled crystallisation in pharmaceutical synthesis and fine chemical production.
Undecanedioic acid is a naturally occurring human metabolite: it has been found in human aortas with advanced atherosclerotic lesions (associated with intercellular matrix macromolecules and specifically with elastin, attributed to increased hydrolysis of esters or decreased esterification) and has been detected in urine from patients under hopantenate therapy during episodes of Reye's-like syndrome; it has also been identified in Polygala tenuifolia root (used as a functional food) and in urban and industrial aerosols of fine particulate matter (PM2.5); it is bioactive against Trichophyton rubrum, T. mentagrophytes, and Microsporum canis at 1 mM concentration.

Chemical Properties of Undecanedioic Acid:
Undecanedioic acid has IUPAC name undecanedioic acid, CAS 1852-04-6, molecular formula C₁₁H₂₀O₄, molecular weight 216.27 g/mol, linear formula HOOC(CH₂)₉COOH, SMILES OC(=O)CCCCCCCCCC(O)=O, InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15), InChIKey LWBHHRRTOZQPDM-UHFFFAOYSA-N; EC 217-440-6; MDL MFCD00004444; BRN 1780537; FDA UNII 7059GFK8NV; ChEBI CHEBI:73713; DTXSID0044862.
Key chemical reactions of undecanedioic acid: (1) polyamide synthesis — melt polycondensation with diamines (hexamethylenediamine, decanediamine, dodecanediamine, various odd-carbon diamines) → even-odd and odd-odd engineering polyamides (Nylon 6,11; 8,11; 10,11; 12,11; 5,11; 7,11; 9,11; 11,11); (2) polyester synthesis — polycondensation with diols → long-chain aliphatic polyesters for coatings, adhesives, and biodegradable plastics; (3) esterification with monohydric alcohols → diester lubricants and plasticisers; (4) salt formation with amines, sodium hydroxide, or ammonium → corrosion inhibitor salts (di-ammonium undecanedioate, sodium undecanedioate); (5) crosslinking with epoxy resins, polyamines, or polyols → adhesive and sealant cure networks; (6) decarboxylation at high temperature; (7) bio-oxidation of undecane or C11 fatty acid derivatives by Candida spp. (ω-oxidation route); (8) synthesis routes: (a) H₅IO₆/CrO₃ oxidation of 11-hydroxyundecanoic acid in CH₃CN/H₂O; (b) α-nitro ketone + NaOH/Oxone in MeOH; (c) Pd-catalysed alkene carbonylation under 50 atm CO at 125°C, 24 h.
Undecanedioic acid is chemically stable under normal ambient conditions; it undergoes the typical reactions of aliphatic dicarboxylic acids — esterification, amidation, salt formation, and reduction; it is a moderately strong dicarboxylic acid (pKa 4.48) and slightly acidic in aqueous solution; it is stable to hydrolysis under ambient conditions; it is incompatible with strong oxidising agents (risk of exothermic reaction), strong bases at elevated temperature (saponification), and reactive amines at elevated temperature (amide bond formation).

Production of Undecanedioic Acid:
Undecanedioic acid is produced commercially by two main routes: (1) bio-fermentation — long-chain alkanes (C11, undecane) or C11 fatty acid derivatives are oxidised by Candida tropicalis or Candida viswanathii yeast strains via ω-oxidation (terminal oxidation mediated by cytochrome P450 monooxygenases), selectively converting both terminal carbons to carboxylic acids while leaving the internal chain intact; the fermentation broth is acidified, filtered, and crystallised to give the product; (2) chemical synthesis routes, including (a) oxidation of 11-hydroxyundecanoic acid with periodic acid (H₅IO₆)/CrO₃ catalyst in aqueous acetonitrile at 0–5°C, followed by recrystallisation from ethyl acetate-hexane; (b) reaction of α-nitro ketone with NaOH/Na₂HPO₄ in methanol at 70°C followed by Oxone oxidation, acidification to pH 2 with HCl, and ethyl acetate extraction; (c) Pd-catalysed carbonylation of an alkene derivative under 50 atm CO, 125°C, 24 h in water/THF, with polycondensation inhibitor and PTSA.H₂O, followed by recrystallisation.
Commercial undecanedioic acid is available in: standard industrial grade (≥98%, white powder or flakes); high-purity grade (≥99.0%); pharmaceutical/analytical grade (≥97–99%); packaging: 25 kg woven-plastic bags lined with PE bag (moisture-proof and dust-proof); 500 kg or 1,000 kg FIBC bags for bulk orders; storage: cool, dry, well-ventilated warehouse, away from direct sunlight, heat, strong oxidisers, and bases; shelf life 24–36 months under recommended conditions.

Undecanedioic Acid Material Safety Data Sheet (MSDS):

Handling of Undecanedioic Acid:
Undecanedioic acid causes serious eye irritation (GHS07, H319); wear safety glasses or face shield, dust mask (N95), and chemical-resistant gloves for all handling operations; avoid generating and inhaling dust; avoid direct contact with skin and eyes; wash hands and exposed skin thoroughly after handling; do not eat, drink, or smoke during handling; the material is a combustible solid — keep away from open flames and strong oxidising agents; use in well-ventilated areas.
At temperatures above the melting point (108–110°C), undecanedioic acid forms a melt; the molten material presents a thermal burn hazard; use appropriate heat-resistant PPE and local exhaust ventilation for hot-melt processing; in case of accidental eye or skin contact, rinse immediately and thoroughly with plenty of water and seek medical advice.

Undecanedioic Acid SDS:

Stability and Reactivity of Undecanedioic Acid:

Chemical stability:
Undecanedioic acid is stable under normal ambient storage and handling conditions.
It is incompatible with strong oxidising agents, strong bases at elevated temperature, and concentrated reactive amines at elevated temperature.

Reactivity:
Undecanedioic acid is a moderately strong aliphatic dicarboxylic acid; it undergoes esterification, amidation, and salt formation under appropriate conditions.
It is a combustible solid (non-flammable at ambient temperature); dust-air mixtures may be explosible if finely divided near ignition sources.

Conditions to avoid:
Strong oxidising agents at elevated temperature.
Open flames and ignition sources above the melting point.
Dust generation near ignition sources.

Incompatible materials:
Strong oxidising agents.
Strong inorganic bases at elevated temperature.
Concentrated reactive amines at elevated temperature.

Hazardous decomposition products:
No hazardous decomposition products under normal ambient conditions.
At high temperatures: CO, CO₂, and low-MW carboxylic acid decomposition products.

Handling and Storage of Undecanedioic Acid:

Handling:
Handle in a well-ventilated area; wear dust mask, safety glasses or face shield, and chemical-resistant gloves.
Avoid dust generation; use local exhaust ventilation for powder handling.
Keep away from open flames, heat sources, and strong oxidising agents.
Wash hands and exposed skin thoroughly after handling; do not eat, drink, or smoke during handling.
In case of eye contact: rinse immediately with plenty of water; seek medical advice.

Storage:
Store in a cool, dry, well-ventilated warehouse away from direct sunlight, heat sources, strong oxidisers, and bases.
Shelf life: 24–36 months under recommended storage conditions.
Sealed in dry conditions at room temperature (long-term storage).
Packaging: 25 kg PE-lined woven-plastic bags; 500/1,000 kg FIBC.

First Aid Measures for Undecanedioic Acid:

Inhalation: Move to fresh air; if dust inhalation causes respiratory irritation, consult a physician.
Skin contact: Rinse with water; wash with soap and water; remove contaminated clothing.
Eye contact: Immediately rinse with plenty of water for at least 15 minutes (remove contact lenses if possible); seek medical attention — causes serious eye irritation (H319).
Ingestion: Rinse mouth; give water to drink; seek medical advice.

Firefighting Measures for Undecanedioic Acid:

Suitable extinguishing media: CO₂, dry chemical, foam, water spray.
Specific hazards: Combustible solid (non-flammable under ambient conditions); dust may form explosive mixtures in air; combustion produces CO and CO₂.
Protective equipment for firefighters: SCBA and full protective clothing.

Accidental Release Measures for Undecanedioic Acid:

Personal precautions: Wear dust mask, gloves, and safety glasses; prevent dust generation.
Environmental precautions: Low environmental hazard at typical quantities; prevent entry into waterways.
Clean-up: Collect by sweeping or vacuuming (wet method preferred to suppress dust); dispose per applicable regulations.

Exposure Controls / Personal Protective Equipment for Undecanedioic Acid:

Engineering controls: Local exhaust ventilation for powder handling and hot-melt processing; general ventilation for routine ambient solid-state handling.
Eye protection: Safety glasses; face shield for powder operations (H319 — serious eye irritation).
Hand protection: Chemical-resistant gloves (nitrile or neoprene).
Respiratory protection: N95 dust mask for powder handling.

Undecanedioic Acid Identifiers:
CAS Number: 1852-04-6
EC Number: 217-440-6
EINECS: 217-440-6
MDL Number: MFCD00004444
BRN (Beilstein/Reaxys): 1780537
PubChem Substance ID: 24850703
FDA UNII: 7059GFK8NV
ChEBI: CHEBI:73713
DTXSID: DTXSID0044862
UNSPSC: 12162002
NACRES: NA.23
IUPAC Name: Undecanedioic acid
Molecular Formula: C₁₁H₂₀O₄
Molecular Weight: 216.27 g/mol
Linear Formula: HOOC(CH₂)₉COOH
SMILES: OC(=O)CCCCCCCCCC(O)=O
InChI: InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)
InChIKey: LWBHHRRTOZQPDM-UHFFFAOYSA-N
pKa: 4.48±0.10 (predicted)
LogP: 2.8 (25°C)
Melting point: 108–110°C (lit.)
Boiling point: 389.33°C (rough estimate)
GHS Classification: GHS07 Warning; H319 (causes serious eye irritation)
REACH: Registered

Properties of Undecanedioic Acid:
Physical state: Solid (crystalline)
Appearance: White to off-white crystalline powder or flakes
Molecular formula: C₁₁H₂₀O₄
Molecular weight: 216.27 g/mol
Melting point: 108–110°C (lit.); 110–114°C (commercial spec)
Boiling point: 389.33°C (rough estimate)
Density: 1.1629 g/cm³ (rough estimate)
Vapour pressure: 10 Pa (20°C)
pKa: 4.48±0.10 (predicted)
LogP: 2.8 (25°C)
Water solubility: 5.10 g/L (21°C, slightly soluble)
Solubility: Methanol, DMSO, ethanol, DMF, diethyl ether
GHS Classification: H319 (causes serious eye irritation)
Polymorphism: Conformational dimorphs (Form I, Form II); solvent-dependent
Storage: Cool, dry, ventilated; sealed; away from oxidants, bases, and heat

Undecanedioic Acid Properties — Specifications:
Product name: Undecanedioic acid (UDDA, DC11)
CAS Number: 1852-04-6
EC Number: 217-440-6
Molecular Formula: C₁₁H₂₀O₄
Molecular Weight: 216.27 g/mol
Appearance: White powder or flakes
Undecanedioic acid content: ≥98%
Total acid: ≥99%
Moisture: ≤0.6%
Iron: ≤10 ppm
Melting point: 110–114°C
GHS: H319 (causes serious eye irritation)
Storage: Cool, dry, ventilated; sealed; away from sunlight, oxidants, bases
Packaging: 25 kg PE-lined woven-plastic bags; 500/1,000 kg FIBC
Shelf life: 24–36 months
Documents: CoA, TDS, SDS

Names of Undecanedioic Acid:
Undecanedioic acid
UDDA
UDA
DC11
1,11-Undecanedioic acid
1,9-Nonanedicarboxylic acid
Hendecanedioic acid
Nonamethylenedicarboxylic acid
Undecandioic acid
Undecanedionic acid
Undecane-1,11-dioic acid
1,9-Nonanedicarboxylate
1,11-Undecanedioate
NSC-400241
NSC 400241
BRN 1780537
MFCD00004444
ChEBI CHEBI:73713
DTXSID0044862
FDA UNII 7059GFK8NV
EINECS 217-440-6
CAS 1852-04-6
Novacid DC11