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terpinyl butyrate

Terpinyl butyrate is a chemical ester used as a flavor and fragrance agent with balsamic and floral sensory characteristics.
Chemical Structure

General Material Description

Terpinyl butyrate, also known as α-terpinyl butyrate, is an ester with the molecular formula C14H24O2. This colorless liquid typically exhibits a sour, fruity balsamic and floral odor along with a bittersweet plum flavor. The compound is identified by several synonyms reflecting its chemical structure, such as butyric acid p-menth-1-en-8-yl ester. Terpinyl butyrate is naturally found in certain essential oils, including cypress, eucalyptus diversicolor, and niaouli. It is widely employed in flavor and fragrance formulations, and detailed chemical and safety information is indexed in major databases like PubChem, which provides structured linking for research and industry reference. Its sensory profile makes it useful for imparting fresh, fruity, floral, and balsamic nuances in perfumery and flavoring applications.

Occurrence, Applicability & Potential Uses

Terpinyl butyrate occurs naturally in essential oils from plants such as cypress, eucalyptus diversicolor, and niaouli. Its scent and flavor characteristics enable its use as a versatile ingredient in flavor and fragrance industries. The compound is applied in perfuming agents and serves as a cypress oil replacer in aromatic blends. According to IFRA (Global) standards, usage restrictions ensure safe incorporation into consumer products. Its flavor applications include enhancing notes reminiscent of apricot, bergamot, plum, and cherry. Additionally, it provides balsamic and fruity facets in formulations designed to mimic natural, fresh outdoors, or woody accords. This ester’s versatility supports its utilization in various product types, including baked goods, beverages, confectionery, and personal care products, respecting the regulatory limits established by FEMA (US) and IFRA.

Physico-Chemical Properties Summary

Terpinyl butyrate is a relatively hydrophobic ester exhibiting a molecular weight of approximately 224.34 g/mol. It has a boiling point range of 244 to 246°C at standard atmospheric pressure and a low vapor pressure of about 0.005 mmHg at 25°C, indicating low volatility under ambient conditions. The compound's specific gravity ranges from 0.962 to 0.968 at 15.5°C, reflecting its liquid state and moderate density. Its estimated log P value of 4.754 suggests significant lipophilicity, influencing its solubility and partitioning behavior in formulations. Terpinyl butyrate is soluble in alcohol but only sparingly soluble in water, which can affect its incorporation method into aqueous or hydrophobic matrices. The flash point is relatively high at 212°F (100°C), indicating moderate flammability risk. These properties dictate cautious handling and formulation considerations in pharmaceutical, cosmetic, and food applications.

FAQ

What is terpinyl butyrate and what are its main sensory characteristics?
Terpinyl butyrate is a chemical ester commonly used as a flavor and fragrance agent. It has a balsamic odor at full concentration, accompanied by sour, rosemary, fruity, balsamic, and floral notes. Its flavor profile includes bittersweet plum nuances. This combination of scent and taste properties makes it valuable for imparting fresh, fruity, and floral aspects in perfumes and flavor formulations.
Where is terpinyl butyrate naturally found and how is it used in industry?
This compound naturally occurs in essential oils of plants such as cypress, eucalyptus diversicolor, and niaouli. Industrially, terpinyl butyrate is utilized as a flavor and fragrance ingredient. It functions as a cypress oil replacement and contributes to complex flavor profiles including apricot, bergamot, cherry, and woody elements. It is commonly incorporated into perfuming agents as well as flavoring preparations for baked goods, beverages, confectionery, and other consumables.
What regulations and safety standards apply to the use of terpinyl butyrate?
Terpinyl butyrate is evaluated under IFRA (Global) standards for fragrance usage, allowing concentrations up to 8% in fragrance concentrates. It is listed by FEMA (US) as GRAS (Generally Recognized As Safe) for flavor use at specified maximum levels in food and beverage categories. While classified as an irritant in some regulatory frameworks, no specific hazard statements are mandated under OSHA (US). Safety data advises avoidance of skin and eye contact and use of appropriate protective equipment during handling.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Perfumer & Flavorists Start search
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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
HMDB (The Human Metabolome Database):HMDB32053
FooDB:FDB008758
Export Tariff Code:2915.60.0000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name terpinyl butyrate
Trivial Name α-Terpinyl butyrate
Short Description p-menth-1-en-8-yl butyrate
Formula C14 H24 O2
CAS Number 2153-28-8
FEMA Number 3049
Flavis Number 9.052
ECHA Number 218-445-6
FDA UNII L94B6AU40N
Nikkaji Number J149.358B
MDL MFCD00083087
COE Number 278
xLogP3-AA 3.20 (est)
NMR Predictor External link
JECFA Food Flavoring 370 terpinyl butyrate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 2153-28-8 ; TERPINYL BUTYRATE
Synonyms
  • butanoic acid 1-methyl-1-(4-methyl-3-cyclohexen-1-yl) ethyl ester
  • butanoic acid, 1-methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl ester
  • butyric acid p-menth-1-en-8-yl ester
  • butyric acid para-menth-1-en-8-yl ester
  • p- menth-1-en-8-ol butyrate
  • para- menth-1-en-8-ol butyrate
  • p- menth-1-en-8-yl butyrate
  • para- menth-1-en-8-yl butyrate
  • methyl methyl cyclohexenyl ethyl butyrate
  • 1-methyl-1-(4-methyl-3-cyclohexen-1-yl) ethyl butyrate
  • 1-methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl butyrate
  • 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl butanoate
  • 2-(4-methylcyclohex-3-en-1-yl)propan-2-yl butyrate
  • alpha terpinyl butyrate
  • terpinyl butyrate natural
  • 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl butanoate
  • Butyric acid, p-menth-1-en-8-yl ester
  • α-Terpinyl butyrate
  • α-Terpineol butyrate
  • 2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl butanoate

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 224.34367370605
Specific gravity @ 15.5 °C
Pounds per Gallon 8.005 to 8.055
Boiling Point 244 to 246°C @ 760 mm Hg
Vapor Pressure 0.005 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 4.754 est
Solubility
alcohol Yes
water, 0.9352 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
sour, rosemary, fruity, balsamic, floral
General comment At 100.00 %. sour rosemary fruity balsamic floral
Flavor Type: Floral
floral, plum, peach, orchid
General comment Bittersweet plum

Occurrences

Potential Uses

Applications
Odor purposes Apricot , Balsam , Banana , Bergamot , Cherry , Cranberry , Currant , Cypress oil replacer , Fresh outdoors , Gooseberry , Heather , Melon , Niaouli , Orchid , Peach , Pine , Plum , Woodruff
Flavoring purposes Chocolate cocoa , Plum greengage plum
Other purposes Gorse , Tweed
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
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.
Oral/Parenteral Toxicity:
Not determined
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 terpinyl butyrate usage levels up to:
8.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 5.10 (μg/capita/day)
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 ppmaverage maximum ppm
baked goods: -9.50000
beverages(nonalcoholic): -6.40000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -210.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -9.20000
fruit ices: -9.20000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -11.00000
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 18 (FGE.18): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical group 6
View page or View pdf

Flavouring Group Evaluation 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):2153-28-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :578423
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl butanoate
Chemidplus:0002153288