1-Dodecanol (112-53-8) Physical and Chemical Properties
1-Dodecanol
A C12 primary fatty alcohol (lauryl alcohol) used as an emollient, surfactant intermediate and solvent component in industrial formulations and R&D.
| CAS Number | 112-53-8 |
| Family | Fatty alcohols (long‑chain primary alcohols, C12) |
| Typical Form | Colorless viscous liquid or white crystalline solid (melting ~24°C) |
| Common Grades | BP, EP, FCC, JP, Reagent Grade, USP |
1-Dodecanol is a saturated, straight-chain primary fatty alcohol of the lauryl series; its molecular formula is \(\ce{C12H26O}\). Structurally it comprises a hydrophobic C12 alkyl chain terminated by a single primary hydroxyl group, giving a molecular architecture that combines a large nonpolar surface area with a single hydrogen-bonding donor/acceptor site. Electronically, the molecule is dominated by the alkyl framework: the hydroxyl oxygen provides a localized polar site but does not delocalize charge across the molecule, so 1-dodecanol behaves as a weakly polar amphiphile rather than a classical small polar solvent.
Because of the long alkyl chain and the single hydroxyl, 1-dodecanol exhibits low aqueous solubility and high lipophilicity, strong surface activity in formulations, and a tendency to partition into organic phases and biological membranes. It undergoes typical alcohol chemistry: reversible proton-transfer acid–base behavior (very weakly acidic), esterification with acids, oxidation (primary alcohol → aldehyde → carboxylic acid under strong oxidizing conditions), and conversion to sulfate/ether derivatives used industrially as surfactants and intermediates. Biochemically it is metabolized by fatty alcohol oxidizing systems and cytochrome P450–dependent hydroxylases to form ω- and (ω‑1)-hydroxylated products and can be oxidized to the corresponding fatty acid (laurate) via alcohol dehydrogenase pathways.
Commercially and industrially 1-dodecanol is a multifunctional intermediate and ingredient in detergents, surfactants (including sulfate esters), lubricants, cosmetics and fragrances, and is used as a flavoring and an agrochemical pheromone component in certain orchard pest-control applications. Common commercial grades reported for this substance include: BP, EP, FCC, JP, Reagent Grade, USP.
Molecular Attributes
Molecular Weight and Composition
- Molecular formula: \(\ce{C12H26O}\).
- Molecular weight: \(186.33\ \mathrm{g}\,\mathrm{mol}^{-1}\) (reported).
- Exact / monoisotopic mass: \(186.198365449\) (reported).
- Heavy atom count: 13; isotope atom count: 0.
- Hydrogen-bonding: HBond donor count = 1; HBond acceptor count = 1.
- Topological polar surface area (TPSA): \(20.2\).
- Rotatable bond count: 10; molecular complexity: 81.2.
These descriptors reflect a single polar functional group on a large hydrophobic scaffold: properties are consistent with a surface-active fatty alcohol that will show limited aqueous solubility and pronounced partitioning into lipophilic matrices.
LogP and Amphiphilicity
- Computed XLogP3: 5.1 (reported).
- Experimental/log Kow reports: log Kow = 5.13 and alternate report 5.4 (reported).
The high logP/logKow values reflect strong hydrophobic character from the C12 chain; however, the terminal hydroxyl confers amphiphilic behavior useful in surfactant and emollient applications. Practical consequences: low water solubility (see solubility entry), strong adsorption to organic phases and suspended solids (high Koc values reported elsewhere), moderate potential for bioconcentration (estimated BCF ≈ 48), and effectiveness as a nonionic surfactant precursor when converted to esters or ethoxylates.
Biochemical Properties
Biosynthesis and Metabolic Context
1-Dodecanol occurs naturally in plant essential oils and as a metabolite in microorganisms and some higher organisms; it can be produced industrially from reduction/hydrogenation of lauric acid or its esters (coconut oil derivatives) or by synthetic routes (Ziegler-type oligomerization/oxo processes followed by hydrogenation). Cellular localization where detected includes extracellular and membrane-associated compartments, consistent with a lipid/alcohol that partitions into membranes and surfaces.
Dermal uptake in experimental conditions is low: after 24-hour covered contact in a mouse model, most of an applied dose remained on the skin surface, with only trace systemic recovery reported, indicating limited percutaneous absorption under those conditions. In liver microsomal systems from various species, metabolism proceeds via cytochrome P450–dependent hydroxylation to ω- and (ω‑1)-hydroxy derivatives and by alcohol-oxidizing systems producing the corresponding fatty acid (laurate); NAD+ (or NADP+) cofactors and P450 isoforms influence rates and regioselectivity.
Reactivity and Transformations
- Typical organic reactivity: esterification with acids (formation of fatty esters), etherification, and oxidation of the primary alcohol to aldehyde and carboxylic acid under appropriate conditions.
- Industrial transformations include sulfation and ethoxylation to yield surfactant derivatives (e.g., sulfate esters, ethoxylates).
- Incompatibilities: strong oxidizing agents — contact can lead to exothermic oxidation and possible hazardous decomposition products.
- Thermal decomposition: when heated to decomposition it emits acrid smoke and fumes (reported).
- Autoignition / flammability: reported autoignition temperatures include 527 °F (275 °C) and 250 °C (reported); flash point reported as 260 °F (127 °C). These values indicate combustible liquid behavior requiring standard precautions for organic combustible materials.
Mechanistically, the alcohol functionality is the reactive center for both enzymatic oxidation in vivo and chemical conversion in processing; the long alkyl chain primarily governs physical partitioning and surface activity rather than reactivity.
Stability and Degradation
Chemical and Enzymatic Degradation Pathways
- Environmental/atmospheric degradation: vapor‑phase reaction with hydroxyl radicals — estimated rate constant corresponds to an atmospheric half-life of about 21 hours for the vapor-phase compound (reported). Direct photolysis is not expected because the compound lacks chromophores absorbing > 290 nm.
- Volatilization / Henry's law: Henry's Law constant reported as 5.186X10-5 atm·m3·mol−1 (reported), indicating potential volatilization from aqueous surfaces under certain conditions. Vapor pressure: 8.48X10-4 mm Hg at 25 \(\,^{\circ}\mathrm{C}\) (reported).
- Aquatic/soil fate: adsorption to suspended solids and sediments is significant (Koc values reported in the thousands), leading to reduced aqueous persistence and attenuation of volatilization from water; estimated BCF ≈ 48 (reported), indicating moderate bioconcentration potential.
- Biodegradation: theoretical/empirical 5‑day BOD values in screening tests ranged from ~20–29.7% and the compound has been described as readily biodegraded under aerobic conditions (reported). Hydrolysis is not a relevant degradation pathway due to lack of hydrolyzable functional groups.
Taken together, 1-dodecanol is subject to biotic oxidation and abiotic atmospheric degradation; environmental persistence is moderated by adsorption and biodegradation, while volatilization can be significant in unconstrained water bodies but attenuated by particulate adsorption.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS RN: 112-53-8
- EC (European Community) number: 203-982-0
- UN Number (transport reference present in supplier data): 3077
- UN Hazard Class (transport reference present in supplier data): 9; Pack Group: III
- UNII: 178A96NLP2
- FEMA Number: 2617
- ChEBI: CHEBI:28878
- ChEMBL: CHEMBL24722
- DrugBank: DB06894
- DSSTox Substance ID: DTXSID5026918
- HMDB: HMDB0011626
Chemical identifiers (structural):
- SMILES: CCCCCCCCCCCCO
- InChI: InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
- InChIKey: LQZZUXJYWNFBMV-UHFFFAOYSA-N
(Identifiers above are reproduced from supplier/registry annotations and analytic records.)
Synonyms and Lipid Nomenclature
Common and historical synonyms reported include: 1‑DODECANOL; Dodecan‑1‑ol; Dodecyl alcohol; Lauryl alcohol; n‑Dodecyl alcohol; Lauroyl alcohol; n‑Lauryl alcohol; C12 alcohol; Lauryl 24; Alcohol C‑12; and related trade/grade names. The compound is also referred to in lipid nomenclature as a C12 primary fatty alcohol (lauryl alcohol).
Industrial and Biological Applications
Roles in Formulations or Biological Systems
1-Dodecanol serves as both a raw-material intermediate and a functional ingredient. Industrial uses include manufacture of sulfate/sulfosuccinate esters and ethoxylates (surfactants and wetting agents), foam stabilizers and defoamers, lubricant additives, emollients and viscosity modifiers in cosmetic formulations, fragrance and flavoring agent (FEMA, JECFA listings), and as a chemical intermediate to produce lauryl derivatives (chlorides, phosphates, thiodipropionates, etc.). It has documented use as a Lepidoptera pheromone/sex attractant in pest-management formulations.
In biological/biochemical contexts it is a naturally occurring lipid component in some plant oils and microbial metabolites and participates in fatty alcohol metabolism where enzymatic oxidation or P450‑mediated hydroxylation converts it to higher‑oxidation-state metabolites (hydroxy‑alcohols and fatty acids).
Production and sourcing: industrial production routes include catalytic hydrogenation of lauric acid or esters derived from coconut oil fatty acids and synthetic routes via Ziegler-type oligomerization/oxo chemistry followed by hydrogenation.
If a concise product/application summary is required but not present above: No concise application summary is available in the current data context; in practice this substance is selected based on its general properties described above.
Safety and Handling Overview
- Physical state and handling: 1-Dodecanol is a colorless liquid at ambient temperatures above its melting/congealing point (melting/congealing reported around \(24\ \,^{\circ}\mathrm{C}\); it may be a solid or crystalline at lower temperatures). It is less dense than water (density ~\(0.8309\) at \(24\ \,^{\circ}\mathrm{C}\)) and will float on water. Vapor pressure and volatility are low at ambient temperature but vapors and mists should be controlled.
- Flammability: combustible liquid; flash point reported as 260 °F (127 °C) (closed cup reported), flammability limits reported as 0.6 to 5.1 vol% (reported), and autoignition temperatures reported as 527 °F (275 °C) and 250 °C (reported). Appropriate fire control agents include alcohol-resistant foam, CO2, or dry chemical; water may be ineffective and can cause frothing in some situations.
- Acute toxicity and irritation: higher alcohols are generally of low acute systemic toxicity by typical industrial exposures but can be skin and eye irritants; inhalation of high concentrations may cause CNS depression. Reported acute toxicity values include LD50 (rat, oral) ≈ 12,800 mg/kg and inhalation LC50 (rat) > 1,050 mg/m3/6 h (reported). Aspiration can cause severe pulmonary effects. Eye irritation and skin irritation have been observed in animal and some human tests depending on concentration and exposure conditions.
- Environmental hazard: harmful/very toxic to aquatic life at mg·L−1 concentrations; avoid release to aquatic environments and follow local regulations for disposal. The substance is biodegradable but can be toxic to aquatic organisms at low mg·L−1 levels.
- First aid basics: for inhalation, move to fresh air and seek medical attention if unwell; for skin contact, remove contaminated clothing and wash with soap and water; for eye contact, rinse thoroughly with water for several minutes and seek medical attention; for ingestion, do not induce vomiting and obtain medical attention—avoid aspiration. These are general precautions; product-specific SDS guidance should be followed for emergency measures.
- Personal protective equipment (PPE) and exposure control: use chemical-resistant gloves, eye/face protection (safety goggles or glasses with side shields), and local exhaust ventilation to limit inhalation/mist generation. Prevent generation of mists and avoid skin and eye contact.
- Storage: recommended to keep tightly closed in a cool, dry, well‑ventilated area; store in containment where runoff to drains is prevented; provisions to contain effluent from fire extinguishing should be available. Avoid strong oxidizers and heat sources.
- Spill and disposal: contain spills, prevent release to drains or waterways, absorb with inert material and collect for recovery or disposal in accordance with local regulations. For large spills, isolate and use diking and appropriate vapor control measures.
For detailed hazard, transport and regulatory information, users should refer to the product‑specific Safety Data Sheet (SDS) and local legislation.
Handling and Storage of Lipid Materials
Because 1‑dodecanol is near its melting point at ambient temperatures in some climates, handling considerations include temperature control for consistent handling properties (liquid vs. solid form), adequate heating or agitation for transfer of solidified material, and dust/mist control if processing generates particulates. Store away from strong oxidizing agents and sources of heat; keep containers tightly closed and located to prevent drainage to sewers or waterways. Implement standard good-practice controls for personal hygiene and waste containment; recycle unused material where feasible and dispose of residues according to environmental regulations.
