Lauric Acid

Basic Information

Name: Lauric Acid

CAS No: Dodecanoic acid [143-07-7]

Functional Categories

Emulsifying agent Food additive Lubricant Surfactant

1. Nonproprietary Names

None adopted.

2. Synonyms

C-1297; dodecanoic acid; dodecoic acid; duodecylic acid; ndodecanoic acid; Hydrofol acid 1255; Hydrofol acid 1295; Hystrene 9512; laurostearic acid; Neo-fat 12; Neo-fat 12–43; Ninol AA62 Extra; 1-undecanecarboxylic acid; vulvic acid; Wecoline 1295

3. Chemical Name & CAS Registry

Dodecanoic acid [143-07-7]

4. Empirical Formula & Molecular Weight

C12H24O2 200.32

5. Structural Formula

6. Applications

Lauric acid is widely used in cosmetics and food products. In pharmaceutical applications it has also been examined for use as an enhancer for topical penetration and transdermal absorption,(1–11) rectal absorption,(12,13) buccal delivery,(14) and intestinal absorption.(15,16) It is also useful for stabilizing oil-in-water emulsions.(17) Lauric acid has also been evaluated for use in aerosol formulations.(18)

7. Description

Lauric acid occurs as a white crystalline powder with a slight odor of bay oil.

8. Pharmacopeial Specifications

See Section 18.

9. Typical Properties

Boiling point 298.98C (at 760 mmHg). Density 0.883 g/cm3 at 208C; 0.8679 g/cm3 at 508C. Dissociation constant pKa= 5.3 at 208C Enthalpy of fusion 36.3 kJ mol–1 Melting point 448C; also reported as 488C. Partition coefficient Log P (octanol : water) = 4.6 Refractive index nD 82 = 1.418; nD 70 = 1.423; nD 50 = 1.4304. Solubility 4.81 mg/mL in water at 258C. Very soluble in ether, ethanol (95%), and methanol; soluble in acetone; slightly soluble in chloroform; miscible with benzene. Specific gravity 0.88 Surface tension 26.6 mN/m at 708C Vapor pressure 10 Pa at 1008C; 100 Pa at 1288C. Viscosity (dynamic) 7.3 mPa s at 508C Viscosity (kinematic) 8.41 mPa s at 508C

10. Stability & Storage

Lauric acid is stable at normal temperatures and should be stored in a cool, dry place. Avoid sources of ignition and contact with incompatible materials.

11. Incompatibilities

Lauric acid is incompatible with strong bases, reducing agents, and oxidizing agents.

12. Method of Manufacture

Lauric acid is a fatty carboxylic acid isolated from vegetable and animal fats or oils. For example, coconut oil and palm kernel oil both contain high proportions of lauric acid. Isolation from natural fats and oils involves hydrolysis, separation of the fatty acids, hydrogenation to convert unsaturated fatty acids to saturated acids, and finally distillation of the specific fatty acid of interest.

13. Safety

Lauric acid is widely used in cosmetic preparations, in the manufacture of food-grade additives, and in pharmaceutical formulations. General exposure to lauric acid occurs through the consumption of food and through dermal contact with cosmetics, soaps, and detergent products. Lauric acid is toxic when administered intravenously. Occupational exposure may cause local irritation of eyes, nose, throat, and respiratory tract,(19) although lauric acid is considered safe and nonirritating for use in cosmetics.(20) No toxicological effects were observed when lauric acid was administered to rats at 35% of the diet for 2 years.(21) Acute exposure tests in rabbits indicate mild irritation.(20) After subcutaneous injection into mice, lauric acid was shown to be noncarcinogenic.(22) LD50 (mouse, IV): 0.13 g/kg(23,24) LD50 (rat, oral): 12 g/kg

14. Handling Precautions

Observe normal precautions appropriate to the circumstances and quantity of material handled. No occupational exposure limits have been established. Under conditions of frequent use or heavy exposure, respiratory protection may be required. When heated, lauric acid emits an acrid smoke and irritating fumes; therefore, use in a well-ventilated area is recommended.

15. Regulatory Status

GRAS listed. Lauric acid is listed as a food additive in the EAFUS list compiled by the FDA. Reported in the EPA TSCA Inventory.

16. Related Substances

Capric acid; myristic acid; palmitic acid; sodium laurate; stearic acid. Capric acid Empirical formula C10H20O2 Molecular weight 172.2 CAS number [334-48-5] Synonyms n-Capric acid; caprinic acid; caprynic acid; carboxylic acid C; decanoic acid; n-decanoic acid; decoic acid; decyclic acid; n-decylic acid; 1-nonanecarboxylic acid. Appearance White to pale yellow crystals with an unpleasant odor. Acid value 320–330 Boiling point 2708C Dissociation constant pKa = 4.9 Melting point 31.58C Partition coefficient Log P (octanol : water) = 4.09 Refractive index nD 40 = 1.4288 Comments Capric acid is used as a flavoring agent in pharmaceutical preparations, providing a citrus-like flavor. It is used in cosmetics as an emulsifying agent. A specification for capric acid is included in the Food Chemicals Codex (FCC).(25) The EINECS number for capric acid is 206-376-4. Sodium laurate Empirical formula C12H23O2Na Molecular weight 222.34 CAS number [629-25-4] Comments Sodium laurate is used as an emulsifying agent and surfactant in cosmetics. The EINECS number for sodium laurate is 211-082-4.

17. Comments

Although not included in any pharmacopeias, a specification for lauric acid is contained in the Food Chemicals Codex (FCC);(26) see Table I. The EINECS number for lauric acid is 205-582-1.