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hexahydrocoumarin
Hexahydrocoumarin is a lactone with a coconut-like odor used mainly for informational purposes but not currently applied as a fragrance or flavor ingredient.
General Material Description
Hexahydrocoumarin, also known by its IUPAC name 3,4,5,6,7,8-hexahydro-2H-1-benzopyran-2-one, is a bicyclic lactone featuring the molecular formula C9H12O2. This compound typically appears as a colorless liquid and is characterized by a distinctive coconut-like odor. It is part of the broader class of coumarin derivatives and shares chemical linkage similarities with chromen-2-one compounds. Hexahydrocoumarin is listed under control vocabularies such as PubChem (CID 69694) and is primarily synthesized for informational and analytical purposes. Although originally examined for use in fragrance and flavor formulations, it is not currently employed commercially in these fields.
Occurrence, Applicability & Potential Uses
Hexahydrocoumarin occurs as a synthetic lactone compound, structurally related to natural coumarins but without known natural biological sources. Its primary application today is for informational and research contexts rather than commercial fragrance or flavor use. Historically, its odor profile was of interest for perfumery and flavoring to provide coconut nuances. However, regulatory guidelines by IFRA (Global) classify hexahydrocoumarin as prohibited in fragrance formulations due to dermal sensitization concerns. Consequently, it holds no authorized use in flavors. Its limited applicability is mostly restricted to experimental and reference scenarios within chemical safety and analytical settings.
Physico-Chemical Properties Summary
Hexahydrocoumarin exhibits a moderate molecular weight of approximately 152.19 g/mol and possesses an estimated logP value near 1.9, indicating moderate lipophilicity suitable for limited solubility in water but appreciable solubility in organic solvents like alcohol. It has a relatively high boiling point range from 294 to 295°C at standard atmospheric pressure, reflecting its low volatility under ambient conditions. The vapor pressure at 25°C is low, about 0.002 mmHg, which correlates with its stable liquid state at room temperature. The compound’s flash point is estimated around 119°C (247°F), supporting safe handling outside immediate ignition sources. These physicochemical parameters influence its limited evaporation rate and suitability for analytical applications rather than open formulation use.
FAQ
What is hexahydrocoumarin and what are its primary characteristics?
Hexahydrocoumarin is a bicyclic lactone compound with the molecular formula C9H12O2. It has a coconut-like odor and is known chemically as 3,4,5,6,7,8-hexahydro-2H-1-benzopyran-2-one. The substance is mainly synthesized for research purposes and appears as a colorless liquid. Although once of interest for fragrance and flavor applications, it is no longer used commercially in these sectors.
Where does hexahydrocoumarin occur and how is it used?
Hexahydrocoumarin is not known to occur naturally in biological sources but is a synthetic derivative related to natural coumarins. Its usage today is limited to informational and analytical contexts, without current commercial application in fragrances or flavors. Due to regulatory prohibitions, it is not employed in consumer products. The compound's distinctive coconut odor was previously considered in perfumery research, but now it primarily serves as a reference chemical.
What regulations affect the use of hexahydrocoumarin and how is it sourced?
Regulatory frameworks such as IFRA (International Fragrance Association, Global) prohibit the use of hexahydrocoumarin as a fragrance ingredient owing to dermal sensitization potential. It is also not authorized for flavor uses. The compound is synthesized chemically, not extracted from natural sources, and is mainly available for research or information purposes. Safety data from agencies like EPA and FDA provide further documentation, though no specific hazard classifications are assigned.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2932.29.6000 |
| ChemSpider: | View |
General Material Information
| Preferred name | hexahydrocoumarin |
| Trivial Name | 3,4,5,6,7,8-Hexahydro-2H-1-benzopyran-2-one |
| Short Description | 2H-1-benzopyran-2-one, 3,4,5,6,7,8-hexahydro- |
| Formula | C9 H12 O2 |
| CAS Number | 700-82-3 |
| ECHA Number | 211-851-4 |
| FDA UNII | 23DDW3J2FU |
| Nikkaji Number | J38.334A |
| xLogP3-AA | 1.30 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| BOC Sciences | Santa Cruz Biotechnology |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 152.19303894043 |
| Boiling Point | 294 to 295°C @ 760 mm Hg |
| Vapor Pressure | 0.002 mmHg @ 25 °C |
| Flash Point TCC Value | 119.44 °C TCC |
| logP (o/w) | 1.89 est |
| Solubility | |
| alcohol | Yes |
| water, 652.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Coconut | |
| coconut, tonka, coumarinic | |
| General comment | At 100.00 %. coconut tonka |
Safety Information
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: | |||
| information only not used for fragrances or flavors | |||
| IFRA Critical Effect: | |||
| Dermal sensitization | |||
| View the IFRA Standard | |||
| Recommendation for hexahydrocoumarin usage levels up to: | |||
| PROHIBITED: Should not be used as a fragrance ingredient. | |||
| Recommendation for hexahydrocoumarin flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :69694 |
| National Institute of Allergy and Infectious Diseases:Data |
| SCCNFP:opinion |
| 3,4,5,6,7,8-hexahydrochromen-2-one |
| Chemidplus:0000700823 |