dextro-fenchone

Dextro-fenchone, also known as (+)-fenchone and identified by its molecular formula C₁₀H₁₆O, is a bicyclic ketone compound belonging to the class of terpenoid ketones. It appears as a colorless to pale yellow liquid and is characterized by a distinctive balsamic, camphoraceous, and pine-like aroma with notable cooling and herbal notes. This compound is naturally present in essential oils from plants such as fennel, anise, star anise, pine, and rosemary. The pure enantiomer (1S,4R)-fenchone exhibits optical activity and is a key ingredient in many flavor and fragrance formulations. Its chemical structure and properties are documented in authoritative sources such as the ChEBI database. Commercially, dextro-fenchone is obtained either by extraction from natural plant oils or synthetic methods designed to produce the optically active form.

Dextro-fenchone occurs naturally in several aromatic plants and spices, including anise seed, star anise fruit and seed, fennel sprout, fennel seed oil, rosemary, and pine. It contributes to the characteristic scent profiles of these botanicals. In industrial applications, dextro-fenchone serves as a flavor and fragrance agent, imparting balsamic, herbal, pine, and cooling characteristics to products. Its versatility encompasses uses in flavoring food items and beverages, as well as in perfumery for its distinctive camphoraceous and woody notes. Regulatory frameworks such as FEMA (US) recognize dextro-fenchone under FEMA number 2479, providing guidelines on its safe usage levels in flavor and fragrance formulations.

Dextro-fenchone exhibits physical and chemical characteristics typical of bicyclic ketones that affect its functionality in formulations. It has a molecular weight of approximately 152.24 g/mol, with moderate volatility demonstrated by a vapor pressure of 0.463 mmHg at 25 °C. Its refractive index ranges from 1.46 to 1.467 at 20 °C, and specific gravity is about 0.94 to 0.948 at 25 °C. The compound melts between 5 and 7 °C and has a boiling point near 63 to 65 °C at reduced pressure (13 mm Hg). Its log P value is around 2.1, reflecting moderate lipophilicity, and it shows good solubility in alcohols and limited solubility in water. These properties support its stability and performance as a fragrance and flavor molecule when properly stored in cool, dry conditions protected from heat and light for up to 24 months or longer.

Leffingwell:	Chirality or Article
	(1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	4695-62-9
Pubchem (cid):	1201521
Pubchem (sid):	134984806

(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
KEGG (GenomeNet):	C09859
HMDB (The Human Metabolome Database):	HMDB34985
FooDB:	FDB014535
Export Tariff Code:	2914.29.5000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 36 - Wear suitable protective clothing.
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.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 6160 mg/kg SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
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 dextro-fenchone usage levels up to:
	9.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU):		6.30 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		5.00 (μg/capita/day)
Threshold of Concern:		540 (μg/person/day)
Structure Class:		II
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: 3
Click here to view publication 3
		average usual ppm	average maximum ppm
baked goods:		-	0.25000
beverages(nonalcoholic):		0.13000	0.80000
beverages(alcoholic):		-	5.00000
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	0.25000
fruit ices:		-	0.25000
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		0.25000	30.00000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
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):

Flavouring Group Evaluation 47, (FGE.47)[1] - Bicyclic secondary alcohols, ketones and related esters from chemical group 8 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf

Flavouring Group Evaluation 87, (FGE.87)[1] - Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47 (2008) - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87 Revision 1 (FGE.87Rev1): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47 (2008) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008) View page or View pdf

Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species View page or View pdf

EPI System: View

EPA Substance Registry Services (TSCA):4695-62-9

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :1201521

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

(1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

Chemidplus:0004695629

RTECS:RB7875200 for cas# 4695-62-9