Dimethyl Sebacate is a versatile diester used as an intermediate in polymer and specialty chemical production.
Dimethyl Sebacate provides flexibility, lubricity and compatibility in selected formulations.
Plasticizers, lubricants, coatings and personal-care products can use Dimethyl Sebacate.
CAS Number: 106-79-6
EC Number: 203-431-4
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
Synonyms: Dimethyl decanedioate, Sebacic acid dimethyl ester, Decanedioic acid dimethyl ester, Dimethyl decane-1,10-dioate, Decanedioic acid 1,10-dimethyl ester, 1,8-Octanedicarboxylic acid bis-methyl ester, Dimethyl octane-1,8-dicarboxylate, Methyl sebacate, DMS, NSC 9415, MFCD00008472, UNII-G87745M355, DTXSID1026740, CHEBI:194205, CHEMBL3186083, AI3-00662, EINECS 203-431-4, CAS 106-79-6
Dimethyl Sebacate has the molecular formula C₁₂H₂₂O₄ and a molar mass of approximately 230.30 g/mol.
The structure of Dimethyl Sebacate contains two methyl ester groups connected by a long hydrocarbon chain.
Also known as dimethyl decanedioate, Dimethyl Sebacate belongs to the aliphatic diester family.
The two ester groups give Dimethyl Sebacate useful reactivity in organic and polymer synthesis.
Dimethyl Sebacate normally appears as a colorless liquid or white crystalline solid depending on temperature.
The melting range of Dimethyl Sebacate lies close to ordinary room temperature.
Water dissolves only a very small amount of Dimethyl Sebacate.
Alcohols, ethers and many organic solvents dissolve Dimethyl Sebacate more readily.
Manufacturers commonly produce Dimethyl Sebacate by esterifying sebacic acid with methanol.
Acid catalysts can accelerate the reaction used to manufacture Dimethyl Sebacate.
Removing water from the esterification system promotes the formation of Dimethyl Sebacate.
Distillation and crystallization can provide Dimethyl Sebacate with controlled purity and color.
Dimethyl Sebacate functions as an intermediate in the production of polymers and specialty chemicals.
The long aliphatic chain of Dimethyl Sebacate can introduce flexibility into resulting materials.
Polyester synthesis can use Dimethyl Sebacate as a difunctional building block.
Transesterification allows Dimethyl Sebacate to react with suitable diols and polyols.
Plasticizer formulations may employ Dimethyl Sebacate to improve polymer flexibility.
Dimethyl Sebacate can contribute to smooth processing and low-temperature performance in selected materials.
Lubricant formulations can use Dimethyl Sebacate as a base component or functional intermediate.
The ester structure of Dimethyl Sebacate supports lubricity and surface-film formation.
Coatings and resin systems may incorporate Dimethyl Sebacate to modify flexibility and flow.
Dimethyl Sebacate can improve compatibility between selected resin and additive components.
Personal-care formulations can use suitable grades of Dimethyl Sebacate as an emollient.
Dimethyl Sebacate can provide a smooth and lightweight feel in oil-based cosmetic systems.
Fragrance formulations may employ Dimethyl Sebacate as a carrier or fixative component.
The low volatility of Dimethyl Sebacate can support the gradual release of fragrance ingredients.
Organic synthesis uses Dimethyl Sebacate as a linear, bifunctional intermediate.
Dimethyl Sebacate can undergo hydrolysis, transesterification and reduction reactions.
Controlled hydrolysis converts Dimethyl Sebacate back into sebacic acid and methanol.
Reduction of Dimethyl Sebacate can produce long-chain functional alcohol intermediates.
Purity, ester value, acidity, water content and color represent important quality parameters for Dimethyl Sebacate.
Chromatographic and spectroscopic methods can confirm the identity and purity of Dimethyl Sebacate.
Uses of Dimethyl Sebacate:
Dimethyl sebacate is used as an internal and external plasticiser for synthetic polymers — particularly polyvinyl chloride (PVC), polyurethanes, cellulose acetate, cellulose nitrate, polylactic acid (PLA), and various rubbers — where it increases flexibility, plasticity, fluidity, workability, impact toughness, and low-temperature performance of the final product by internal modification (dissolution) of the polymer molecule, or by external surface treatment to impart flexibility without chemical reaction with the polymer backbone.
Dimethyl sebacate is used as a transesterification starting material for the synthesis of bis(2-ethylhexyl) sebacate (DOS, dioctyl sebacate) — a premium, long-chain aliphatic diester plasticiser and synthetic ester base oil used in petroleum-based and synthetic lubricants, specialty greases, aerospace hydraulic fluids, and flexible PVC compounds requiring excellent low-temperature performance (down to −60°C); DMS + 2-ethylhexanol → DOS + 2 methanol (acid or base catalyst).
Dimethyl sebacate is used as a chemical intermediate in the synthesis of decanedihydrazide (sebacic dihydrazide), a versatile crosslinker and chain extender that serves as a precursor for isocyanates and thermoplastic polyurethanes; DMS also serves as a starting material for the preparation of polytetramethylene sebacate, an engineering polyester elastomer used in flexible fibres, films, and coatings.
Dimethyl sebacate is used as a specialised high-boiling industrial solvent (boiling point ~294°C) in chemical formulations requiring a biodegradable, low-toxicity, high-solvency, non-volatile carrier — including floor coatings, maintenance coatings, industrial cleaning concentrates, lubricant formulations, and specialty resin solutions; its long aliphatic chain provides excellent compatibility with oils and non-polar polymers.
Dimethyl sebacate is used as a textile softener and conditioner — it is classified under the softener/conditioner and emollient category — improving the hand, softness, pliability, and mechanical processing of natural and synthetic fabrics; in personal care and cosmetic formulations it is used as an emollient, skin-conditioning agent, and carrier solvent for active ingredients.
Dimethyl sebacate is used as a fragrance and flavour ingredient; it has a fruity, estery character and is used in fine fragrances, cosmetics, soaps, and detergents as a modifier and fixative; it is also used in food flavour formulations as a fruity, waxy, fatty note contributor.
Dimethyl sebacate is used as a synthetic building block in the production of UV stabilisers (including hindered amine light stabilisers, HALS, based on the sebacate backbone), dyes, pharmaceutical intermediates, and specialty long-chain esters; it was used in the biosynthesis of oligomeric sebacates and lubricant oils, as a convenient starting material for cyclization of N-succinylglycine dimethyl ester, and for conversion to cyclodecanediol by acyloin condensation followed by hydrogenation with a copper chromite catalyst.
Dimethyl sebacate is used in the antirust lubricating oil industry as a co-additive to increase the antirust properties of lubricating oils on metals — the sebacate ester backbone provides an adsorbed film on metal surfaces; it is also used in hydraulic fluids, candle manufacture, and as a surfactant component in emulsifier systems where its natural, plant-derived origin from castor oil is valued.
Benefits and Advantages of Dimethyl Sebacate:
Dimethyl sebacate is derived from sebacic acid, which is produced commercially from castor oil (a renewable, non-food-competing bio-based feedstock grown in arid and semi-arid regions), providing a naturally sourced, bio-based supply chain for a plasticiser and solvent with a significantly reduced carbon footprint compared with fully petrochemical alternatives; this origin aligns with EU Green Deal, circular economy, and bio-content requirements.
Dimethyl sebacate has an exceptionally low acute toxicity (No GHS classification, no signal word), is not classified as an endocrine disruptor, SVHC, or CMR substance, and is compliant with REACH and applicable FDA food-contact regulations — making it a preferred safer alternative to phthalate plasticisers (DEHP, DBP, BBP) and other regulated compounds in sensitive applications including toys, food packaging, medical devices, and personal care products.
The long C₁₀ aliphatic backbone of dimethyl sebacate provides superior low-temperature flexibility (plasticised PVC films remain flexible well below 0°C), low volatility, good permanence in polymer matrices (low migration and extraction), and excellent compatibility with oils, waxes, and non-polar polymers — a set of properties difficult to achieve with shorter-chain (C₄–C₆) diester plasticisers.
Dimethyl sebacate is a high-value precursor to bis(2-ethylhexyl) sebacate (DOS) and other long-chain sebacate esters via one-step transesterification, providing a reactive intermediate platform that can be converted into the target ester in a single operation without isolating the acid form — a process advantage over direct esterification from sebacic acid in many manufacturing settings.
Features of Dimethyl Sebacate:
Dimethyl sebacate is a clear, colourless to very pale yellow, low-viscosity liquid with a faint, pleasant fruity-estery odour; it is liquid at room temperature with a low melting point; boiling point ~294°C at 760 mmHg (reported values: 215–220°C at 14 mmHg; 156–160°C at 3 mmHg); density approximately 0.988 g/cm³ at 20°C; refractive index n20/D ~1.435; flash point ~163°C (est.); vapour pressure very low at ambient temperature.
Dimethyl sebacate is sparingly soluble in water; miscible with common organic solvents including ethanol, acetone, chloroform, diethyl ether, benzene, toluene, and most oils; XLogP3 ~2 indicating moderate lipophilicity; TPSA 52.6 Ų; rotatable bond count 11 (providing the chain conformational flexibility responsible for plasticising action); no hydrogen bond donors; 4 hydrogen bond acceptors (two ester oxygens + two carbonyl oxygens).
Key molecular structure features: straight-chain, linear symmetric C₁₂ diester; longest carbon chain (C₁₀ dicarboxylate = sebacic acid unit); two terminal methyl ester groups (−COOCH₃); the long aliphatic spacer provides low Tg, high chain mobility, good solvency for non-polar matrices, and serves as a versatile platform for transesterification to higher dialkyl sebacates (DOS, dibutyl sebacate, etc.).
Sebacic acid, the parent diacid, is a naturally occurring dicarboxylic acid also found in human skin sebum; human neutrophils can convert sebacic acid to its 5-oxo analog (5-oxo-6E,8Z-octadecenoic acid), a potent activator of eosinophils and monocytes via the OXER1 receptor — the natural skin origin of sebacic acid confers intrinsic biocompatibility and skin affinity to dimethyl sebacate that is leveraged in cosmetic formulations.
Chemical Properties of Dimethyl Sebacate:
Dimethyl sebacate has IUPAC name dimethyl decane-1,10-dioate, linear formula CH₃OOC(CH₂)₈COOCH₃, SMILES COC(=O)CCCCCCCCC(=O)OC, InChI=1S/C12H22O4/c1-15-11(13)9-7-5-3-4-6-8-10-12(14)16-2/h3-10H2,1-2H3, InChIKey WNLRTRBMVRJNCN-UHFFFAOYSA-N; PubChem CID 68143; CHEBI:194205; MFCD00008472; UNII G87745M355; DTXSID1026740; CHEMBL3186083; NSC 9415.
Dimethyl sebacate undergoes the characteristic reactions of an aliphatic long-chain diester: (1) transesterification with higher alcohols (2-ethylhexanol, n-butanol, 2-propanol) in the presence of acid or base catalysts → higher dialkyl sebacates (DOS, DBS, etc.) + methanol; (2) saponification with NaOH or KOH → disodium/dipotassium sebacate + methanol; (3) aminolysis with hydrazine → sebacic dihydrazide (used as polyurethane crosslinker); (4) acyloin condensation under base → cyclodecane-1,2-diol precursor; (5) reduction with LiAlH₄ or NaBH₄ → 1,10-decanediol + methanol; (6) acid hydrolysis → sebacic acid + methanol.
Dimethyl sebacate is produced by direct esterification of sebacic acid with excess methanol in the presence of H₂SO₄, p-toluenesulfonic acid, or heterogeneous acid catalyst (ion-exchange resin, zeolite) at 60–100°C with azeotropic or molecular-sieve water removal; alternatively by transesterification of higher sebacate esters with methanol; sebacic acid is obtained from castor oil by alkaline cleavage of ricinoleic acid (the main fatty acid of castor oil) in industrial NaOH/KOH pressure-cracking processes, with octanol and glycerol as co-products.
Dimethyl sebacate is stable under normal ambient storage conditions; incompatible with strong bases (saponification), strong acids at elevated temperature, and strong oxidising agents; it does not polymerise under normal conditions; GHS: Not Classified (no signal word, no acute toxicity classification); no SVHC, no CMR classification; REACH registered; compliant with applicable FDA food-contact regulations.
Production of Dimethyl Sebacate:
Dimethyl sebacate is produced commercially by direct esterification of sebacic acid with methanol (molar ratio ~1:5) in the presence of a strong acid catalyst (concentrated H₂SO₄, p-TsOH, or solid acid catalyst) at 65–90°C with continuous water removal; the product is purified by neutralisation, washing, drying, and vacuum distillation; purity ≥95–99% is achievable; sebacic acid feedstock is produced from castor oil (the world's major commercial route, primarily in India and China).
Commercial dimethyl sebacate is available at ≥95% (technical), ≥98% (pure), ≥99% (high purity), and analytical standard grades as a colourless clear liquid; specification limits: assay ≥98%; refractive index n20/D 1.434–1.436; density 0.984–0.990 g/cm³; acid value ≤1.0 mgKOH/g; colour (APHA) ≤10; water content ≤0.1%; packaging: 200 kg steel drum; IBC; bulk tank.
Dimethyl Sebacate Material Safety Data Sheet (MSDS):
Handling of Dimethyl Sebacate:
Dimethyl sebacate is not classified as hazardous under GHS (no signal word, low acute toxicity); standard chemical handling precautions apply: avoid prolonged or repeated skin and eye contact; use in well-ventilated areas; avoid generation of aerosols or mists at elevated temperatures; wear appropriate PPE (gloves, safety glasses) for routine handling.
Dimethyl sebacate has very low vapour pressure at ambient temperature, minimising inhalation exposure risk during normal handling; flash point ~163°C makes it non-flammable under ambient conditions; standard industrial and laboratory hygiene practices are sufficient for routine handling.
Dimethyl Sebacate SDS:
Stability and Reactivity of Dimethyl Sebacate:
Chemical stability:
Dimethyl sebacate is chemically stable under normal ambient storage and handling conditions.
Dimethyl sebacate undergoes slow hydrolysis in the presence of water and strong acids or bases; it is susceptible to saponification by strong alkali.
Reactivity:
Dimethyl sebacate undergoes transesterification with alcohols in the presence of acid or base catalysts.
Dimethyl sebacate is incompatible with strong bases (saponification), strong oxidising agents, and strong acids at elevated temperature.
Conditions to avoid:
Strong bases (saponification — formation of disodium sebacate + methanol).
Strong acids at elevated temperature.
Strong oxidising agents.
No fire hazard under ambient conditions (flash point ~163°C).
Incompatible materials:
Strong alkali (NaOH, KOH) — saponification.
Strong mineral acids at elevated temperature.
Strong oxidising agents (peroxides, permanganates).
Reactive metals at elevated temperature.
Hazardous decomposition products:
Carbon monoxide (CO) and carbon dioxide (CO₂) upon combustion.
Methanol vapour upon thermal decomposition or hydrolysis.
Handling and Storage of Dimethyl Sebacate:
Handling:
Use in well-ventilated areas; no special ignition precautions required at ambient temperature.
Wear gloves and safety glasses for routine handling; avoid prolonged skin contact.
Standard laboratory and industrial hygiene practices are sufficient.
Wash hands after handling; do not eat, drink, or smoke in work areas.
Storage:
Store in tightly closed containers in a cool (below 30°C), dry, well-ventilated area.
Keep away from strong alkalis and oxidising agents.
No fire hazard classification for ambient storage; no special transport requirements.
Packaging: 200 kg steel drum; IBC; bulk tank.
First Aid Measures for Dimethyl Sebacate:
Inhalation:
Move the affected person to fresh air; if symptoms persist, consult a physician.
Under normal ambient conditions, vapour exposure is negligible (very low vapour pressure).
Skin contact:
Wash with soap and water; remove contaminated clothing.
Prolonged or repeated contact may cause mild irritation; consult a physician if irritation persists.
Eye contact:
Rinse with plenty of water for at least 15 minutes.
Seek medical attention if irritation persists.
Ingestion:
Rinse the mouth with water; consult a physician; dimethyl sebacate has very low acute oral toxicity.
Firefighting Measures for Dimethyl Sebacate:
Suitable extinguishing media:
CO₂, dry chemical, alcohol-resistant foam, water spray; suitable for class B fire.
Specific hazards:
Dimethyl sebacate is a combustible liquid at elevated temperature (flash point ~163°C); vapours are heavier than air; combustion produces CO and CO₂; no unusual fire hazard at ambient temperature.
Protective equipment for firefighters:
SCBA and full protective clothing; cool containers with water spray.
Accidental Release Measures for Dimethyl Sebacate:
Personal precautions:
Wear appropriate PPE; ventilate area; eliminate ignition sources if large quantities are heated.
Environmental precautions:
Dimethyl sebacate is biodegradable and has low environmental toxicity; prevent large quantities from entering water courses.
Clean-up methods:
Absorb with inert material (vermiculite, sand); collect in closed containers; dispose as non-hazardous chemical waste per applicable regulations.
Exposure Controls / Personal Protective Equipment for Dimethyl Sebacate:
Engineering controls:
Good general ventilation; local exhaust at elevated processing temperatures; standard laboratory and industrial practice.
Eye protection: Safety glasses or goggles.
Hand protection: Nitrile or neoprene gloves for prolonged contact.
Respiratory protection: None required under normal ambient conditions; organic vapour cartridge for hot processing.
Dimethyl Sebacate Identifiers:
CAS Number: 106-79-6
EC Number: 203-431-4
REACH: 01-2119438365-XXXX
MDL Number: MFCD00008472
PubChem CID: 68143
CHEBI: 194205
CHEMBL: CHEMBL3186083
DTXSID: DTXSID1026740
UNII: G87745M355
NSC: 9415
IUPAC Name: Dimethyl decane-1,10-dioate
Linear Formula: CH₃OOC(CH₂)₈COOCH₃ (C₁₂H₂₂O₄)
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
Exact Mass: 230.15180918 Da
SMILES: COC(=O)CCCCCCCCC(=O)OC
InChI: InChI=1S/C12H22O4/c1-15-11(13)9-7-5-3-4-6-8-10-12(14)16-2/h3-10H2,1-2H3
InChIKey: WNLRTRBMVRJNCN-UHFFFAOYSA-N
XLogP3: 2 (estimated)
TPSA: 52.6 Ų
HBA: 4; HBD: 0; Rotatable bonds: 11; Heavy atoms: 16; Complexity: 179
GHS Signal Word: None (Not Classified)
GHS Classification: Not Classified (no acute toxicity, no CMR, no SVHC)
Flash point: ~163°C (estimated)
Boiling point: ~294°C (760 mmHg); ~215°C (14 mmHg)
Origin: Bio-based (castor oil derived)
Properties of Dimethyl Sebacate:
Physical state: Liquid
Appearance: Clear, colourless to very pale yellow liquid
Odour: Faint, pleasant, fruity-estery
Molecular formula: C₁₂H₂₂O₄
Molecular weight: 230.30 g/mol
Boiling point: ~294°C (760 mmHg); 215–220°C (14 mmHg)
Flash point: ~163°C
Density: ~0.988 g/cm³ at 20°C
Refractive index: n20/D ~1.435
Vapour pressure: Very low at ambient temperature
Water solubility: Sparingly soluble
Organic solvent solubility: Miscible with ethanol, acetone, chloroform, ether, benzene, oils
XLogP3: 2
TPSA: 52.6 Ų
GHS Classification: Not Classified
Origin: Bio-based (castor oil)
Storage: Below 30°C; tightly closed; away from strong bases and oxidants
Dimethyl Sebacate Properties — Specifications:
Product name: Dimethyl sebacate (DMS)
CAS Number: 106-79-6
EC Number: 203-431-4
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
Purity: ≥95% (technical); ≥98% (pure); ≥99% (high purity); analytical standard
Acid value: ≤1.0 mgKOH/g
Refractive index: n20/D 1.434–1.436
Density: 0.984–0.990 g/cm³ (20°C)
Colour (APHA): ≤10
Water content: ≤0.1%
Appearance: Clear, colourless liquid
Boiling point: ~294°C (760 mmHg)
Flash point: ~163°C
GHS Classification: Not Classified
Origin: Bio-based (castor oil derived)
Storage: Below 30°C; tightly closed; cool, dry, ventilated
Packaging: 200 kg steel drum; IBC; bulk tank
Documents: CoA (Certificate of Analysis), MSDS/SDS available
Names of Dimethyl Sebacate:
Dimethyl sebacate
Dimethyl decanedioate
Sebacic acid dimethyl ester
Decanedioic acid dimethyl ester
Dimethyl decane-1,10-dioate
Decanedioic acid 1,10-dimethyl ester
1,8-Octanedicarboxylic acid bis-methyl ester
Dimethyl octane-1,8-dicarboxylate
Methyl sebacate
DMS
NSC 9415
MFCD00008472
UNII G87745M355
DTXSID1026740
CHEBI 194205
CAS 106-79-6
EINECS 203-431-4