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(+)-alpha-campholenic aldehyde
(+)-Alpha-campholenic aldehyde is a naturally occurring flavor and fragrance compound known for its herbal, green aroma and use in various essential oils and perfumery.
General Material Description
(+)-Alpha-campholenic aldehyde, with the molecular formula C10H16O, is a chiral aldehyde used predominantly in flavor and fragrance applications. Known also as alpha-Campholenal and by various synonyms including aromavert, this compound exhibits a characteristic herbal and green odor with woody, amber, and leafy facets. Its sensory profile includes green, spicy, and herbal notes reminiscent of chrysanthemum and cilantro. The compound is referenced under PubChem CID 1252759 and is typically sourced from natural essential oils such as eucalyptus, labdanum, and juniper berry. It is a colorless to pale liquid utilized in perfuming agents and flavor formulations where its distinctive green note is valued.
Occurrence, Applicability & Potential Uses
(+)-Alpha-campholenic aldehyde is found naturally in several essential oils including cistus oil, eucalyptus globulus oil, labdanum oil, juniper berry oil, and others typically at trace to low percentage levels. Its significant presence in eucalyptus leaf oils, sometimes reaching 4%, suggests a role in the characteristic aroma of those plant extracts. The compound's contribution to herbal, woody, and green notes makes it suitable for flavor and fragrance industries as a key aroma chemical. It is employed according to FEMA (US) guidelines for flavoring substances and recommended for use up to 5% in fragrance concentrates based on IFRA (Global) standards. Typical use cases include adding green, citrus, woody, herbal, and spicy odor impressions in perfumes, and it serves as a cassie absolute replacer and citrus/spice flavor enhancer in food products.
Physico-Chemical Properties Summary
(+)-Alpha-campholenic aldehyde possesses a molecular weight of approximately 152.24 g/mol and a molecular formula of C10H16O. It exhibits moderate volatility with a boiling point range of 83 to 84°C at 1 mm Hg pressure. The compound has a refractive index between 1.462 and 1.469 measured at 20°C, and a specific gravity ranging from 0.918 to 0.926 at 25°C. Its vapor pressure at 25°C is about 0.415 mmHg, indicating moderate evaporation tendencies suitable for fragrance applications. Solubility is observed in alcohols and water (estimated at 111.2 mg/L at 25°C). The estimated log P value of 2.59 supports moderate lipophilicity relevant to formulation behavior. Safety data indicates a flash point near 151°F (66°C). These physico-chemical characteristics influence its stability, volatility, and suitability for use in various aromatic compositions.
FAQ
What is (+)-alpha-campholenic aldehyde and what are its main characteristics?
(+)-Alpha-campholenic aldehyde is an organic compound classified as an aldehyde with the formula C10H16O. It is recognized for its herbal, green, woody, and amber odor qualities, making it valuable in flavor and fragrance formulations. The compound has a chiral center giving it specific stereoisomeric properties. It occurs naturally in several essential oils such as eucalyptus and labdanum, contributing distinct sensory notes used in perfumes and flavorings.
In which natural sources does (+)-alpha-campholenic aldehyde occur, and how is it typically used in industry?
This aldehyde is identified in various essential oils, including eucalyptus globulus oil, cistus oil, labdanum oil, and juniper berry oil, generally in trace amounts to low percentages. Its presence in these natural extracts imparts characteristic herbal and woody aromas. Industrially, (+)-alpha-campholenic aldehyde is used as a flavoring and fragrance agent, offering green, citrus, and spicy notes. It serves as a replacement for cassie absolute in perfumery and enhances flavor complexity in food applications, conforming to guidelines set by entities such as FEMA (US) and IFRA (Global).
What regulatory standards and safety information apply to (+)-alpha-campholenic aldehyde?
(+)-Alpha-campholenic aldehyde is regulated under FEMA (US) where it holds FEMA number 3592 and is classified as generally recognized as safe (GRAS) for use in flavorings. The IFRA (Global) code of practice recommends usage up to 5% in fragrance concentrates. Toxicological studies show relatively low oral toxicity with LD50 values approximately 4100 to 4300 mg/kg in rats. No significant occupational hazard classifications or precautionary GHS statements are currently assigned. Its inclusion in JECFA’s flavoring list supports its safety profile when used within established limits. Manufacturers should refer to these standards to ensure compliance.
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 |
Literature & References
| Leffingwell: | Chirality or Article |
| 2-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 4501-58-0 |
| Pubchem (cid): | 1252759 |
| Pubchem (sid): | 134984169 |
| Pherobase: | View |
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 |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB34973 |
| FooDB: | FDB019631 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | (+)-alpha-campholenic aldehyde |
| Trivial Name | α-Campholenal |
| Short Description | (1R)-2,2,3-trimethylcyclopent-3-en-1-yl acetaldehyde |
| Formula | C10 H16 O |
| CAS Number | 4501-58-0 |
| Deleted CAS Number | 42370-35-4 |
| FEMA Number | 3592 |
| Flavis Number | 5.119 |
| ECHA Number | 224-815-8 |
| FDA UNII | 75LU5216DI |
| Nikkaji Number | J100.021G |
| COE Number | 10325 |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 967 2,2,3-trimethylcyclopent-3-en-1-yl acetaldehyde |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4501-58-0 ; 2,2,3-TRIMETHYLCYCLOPENT-3-EN-1-YL ACETALDEHYDE |
| Synonyms |
|
Suppliers
| BOC Sciences | Ernesto Ventós |
| Foreverest Resources | Indukern F&F |
| Lluch Essence | Parchem |
| Penta International | Indukern, S.A. F&F Ingredients Division |
| Penta International Corporation | Ernesto Ventós S.A. |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 152.23672485352 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.639 to 7.705 |
| Refractive Index | 1.462 to 1.469 @ 20 °C |
| Boiling Point | 83 to 84°C @ 1 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.415 mmHg @ 25 °C |
| Flash Point TCC Value | 66.11 °C TCC |
| logP (o/w) | 2.587 est |
| Solubility | |
| alcohol | Yes |
| water, 111.2 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Herbal | |
| herbal, green, woody, amber, leafy | |
| Odor strength | high , recommend smelling in a 10.00 % solution or less |
| Substantivity | 8 hour(s) at 100.00 % |
| Luebke, William tgsc, (1988) | At 10.00 % in dipropylene glycol. herbal green woody amber leafy |
| Flavor Type: Green | |
| green, spicy, herbal, chrysanthemum, leafy, cilantro, woody | |
| Luebke, William tgsc, (1988) | Green spicy herbal chrysanthemum leafy cilantro woody |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Amber , Blackberry , Cassie absolute replacer , Chrysanthemum , Citrus , Green , Green leaf , Herbal , Mango , Mango flower , Neroli , Woody |
| Flavoring purposes | Cassie absolute replacer , Citrus , Spice |
| Other purposes | Ciltrano , Leaf , Leafy , Spicy |
| Cosmetic purposes | Perfuming agents |
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: | |
| oral-rat LD50 4300 mg/kg The LD50 value cited is deduced according to Litchfield & Wilcoxon, 1949. Another LD50 value is also cited in the BIBRA study, 3900 mg/kg, deduced according to Weill, 1952. (BIBRA, 1976) oral-rat LD50 4100 mg/kg Study acceptable. Substance name is given as aldehyde campholenique. (Moreno, 1978h) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and 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 (+)-alpha-campholenic aldehyde usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 5.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | ND (μg/capita/day) | ||
| Threshold of Concern: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 8.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | 5.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 5.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | 5.00000 | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 12 (FGE.12); Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 - Flavouring Group Evaluation 12, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 73, (FGE.73)[1] - Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde and esters evaluated by EFSA in FGE.12 (2005) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 1 (FGE.73Rev1): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters evaluated by EFSA in FGE.12Rev2 (2011) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 2 (FGE.73Rev2): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev3 (2012) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 3 (FGE.73Rev3): Consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev4 (2013) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 4 (FGE.73Rev4): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev5 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 5 (FGE.73Rev5): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th, 63rd and 86th meeting) and structurally related to substances evaluated in FGE.12Rev5 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):4501-58-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :1252759 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| 2-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde |
| Chemidplus:0004501580 |