pinoacetaldehyde

Pinoacetaldehyde, also known by the trivial name homonopal and IUPAC designation 6,6-dimethyl-2-norpinene-2-propionaldehyde, is a bicyclic aldehyde with the molecular formula C₁₂H₁₈O. It is recognized for its fresh and clean aldehydic scent complemented by pine, herbal, and balsamic notes. This compound is predominantly employed in fragrance formulations to impart a woody and marine character reminiscent of natural pine and sea breeze aromas. The chemical structure includes a bicyclo[3.1.1]hept-2-ene backbone substituted with dimethyl groups, contributing to its distinctive sensory profile. Pinoacetaldehyde links to controlled vocabulary entries such as PubChem CID 118111. It is generally sourced via synthetic routes tailored to provide the desired purity for flavor and fragrance applications.

Pinoacetaldehyde is not commonly found as a natural metabolite but is utilized extensively within the fragrance industry due to its aldehydic and fresh sensory properties. It imparts green, herbal, and melon-like nuances in addition to pine and clean ozone topnotes, making it valuable for complex perfume compositions. Its utility as a perfuming agent aligns with standards, including IFRA (Global), which regulates maximum usage levels to ensure consumer safety. The International Fragrance Association recommends limits of up to 2.0% in fragrance concentrates. Applications center on formulations requiring medium substantivity and a fresh woody character, particularly in marine-inspired and natural pine accords.

Pinoacetaldehyde exhibits physical and chemical properties characteristic of moderately hydrophobic aldehydes with a molecular weight near 178.3 g/mol. Its boiling point ranges between 243 and 244 °C at standard atmospheric pressure, indicating moderate thermal stability for fragrance formulation processes. Specific gravity lies between 0.951 and 0.958 at room temperature (20–25 °C), and its refractive index varies from 1.481 to 1.486 at 20 °C. The vapor pressure is low, around 0.03 mmHg at 25 °C, contributing to its substantivity in perfumes. Its octanol-water partition coefficient estimation (logP) is 3.4, denoting moderate lipophilicity impacting solubility and penetration in formulations. The compound is soluble in alcohol, compatible with typical fragrance solvents but shows limited water solubility. A flash point near 89 °C (192 °F) discourages volatility-related hazards under normal handling conditions.

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
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(IUPAC):	Periodic Table of the Elements
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Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for pinoacetaldehyde usage levels up to:
	2.0000 % in the fragrance concentrate.
Recommendation for pinoacetaldehyde flavor usage levels up to:
	not for flavor use.

Safety references

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):33885-51-7

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :118111

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

3-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)propanal

Chemidplus:0033885517