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1,4-Cineole

1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane

Isocineole · 1,4-Epoxy-p-menthane

Bicyclic monoterpenoid ether · C₁₀H₁₈O

Chemical structure of 1,4-Cineole
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
470-67-7
Molecular formula
C₁₀H₁₈O
Molecular weight
154.25 g/mol
Aroma
Soft camphoraceous, cool, faintly woody, milder than 1,8-cineole.

Safety

Low concern · Safe at standard use

1,4-Cineole is the minor isomer of 1,8-cineole. The compound appears at low concentrations in a few citrus and cypress oils.

Skin. A 16 percent patch test on 25 volunteers caused no irritation or sensitization.

Oral and dermal. Acute oral LD50 in rats is 3.1 g/kg; rabbit dermal LD50 is under 5 g/kg.

Limited data but no specific risk indicated.

Usage guidelines

Concern level
Low
Oils with high content
Distilled lime 2.0–3.0 percent · Port Orford cedarwood 1.3 percent

Found in essential oils

Principal sources
Lime (distilled)1.8 – 3.0 %
Cedarwood (Port Orford)1.3 %

Pharmacokinetics

1,4-Cineole given orally to rabbits at 2 g/animal yielded five urinary metabolites: 9-hydroxy-1,4-cineole (most abundant), 1,4-cineole-9-carboxylic acid, 1,4-cineole-8-en-9-ol, 3,8-dihydroxy-1,4-cineole and 8,9-dihydroxy-1,4-cineole. CYP3A4 in rat and human liver microsomes generates 2-exo-hydroxy-1,4-cineole as a major metabolite.

Notes

1,4-Cineole contributes a soft camphor freshness to a few distilled citrus oils.