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bornyl benzoate

Bornyl benzoate is an ester known for its pine balsam and herbal odor notes, primarily investigated for fragrance applications but not widely used in commercial flavor or fragrance products.

General Material Description

Bornyl benzoate is an ester compound derived from borneol and benzoic acid, featuring the IUPAC name [(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] benzoate. It appears as a colorless to pale yellow liquid with low intensity pine and balsam odor notes, accompanied by a subtle herbal character. The molecular formula is C17H22O2, and its molecular weight is approximately 258.36 g/mol. Classified as a bicyclic ester, it relates structurally to borneol derivatives used in aroma chemistry. Bornyl benzoate is primarily sourced via chemical synthesis from borneol and benzoic acid. It is documented under PubChem entry CID 6428443, providing a detailed overview of its physical and chemical data as well as literature references.

Occurrence, Applicability & Potential Uses

Bornyl benzoate occurs predominantly as a synthetic derivative rather than a natural product. Its pine and balsam odor characteristics make it a compound of interest in fragrance research, particularly for woody and herbal accords. Despite its sensory properties, bornyl benzoate is not commonly employed in commercial fragrances or flavor formulations. Regulatory evaluation under standards such as FEMA (US) classifies it for information purposes only, with no recommended uses in flavor or fragrance products. Its physicochemical profile and odor profile suggest potential, albeit limited, application in experimental aroma chemical studies rather than mainstream use.

Physico-Chemical Properties Summary

Bornyl benzoate is characterized by a high boiling point of approximately 328 to 329°C at standard atmospheric pressure (760 mm Hg), indicating strong intermolecular interactions and thermal stability. It exhibits a low vapor pressure near 0.000184 mmHg at 25°C, reflecting low volatility and limited evaporation under ambient conditions. The compound has an estimated log P of 5.365, indicating significant lipophilicity and solubility in nonpolar solvents such as alcohols while showing minimal water solubility. Its flash point exceeds 149°C (300°F), making it relatively safe regarding flammability in typical handling scenarios. These properties influence its handling, storage, and potential formulation roles, favoring use in systems requiring stable, low-volatility aroma components.

FAQ

What is bornyl benzoate and what are its key odor characteristics?
Bornyl benzoate is a bicyclic ester formed from borneol and benzoic acid. It is noted for its pine balsam and herbal odor profile, although the scent intensity is relatively low. The compound is primarily of interest for its aromatic properties in research rather than commercial fragrance applications.
Where does bornyl benzoate occur and how is it applied?
Bornyl benzoate does not typically occur naturally and is obtained through chemical synthesis. Its usage is limited to informational purposes in fragrance research due to its specific odor qualities. It is not commonly used in commercial fragrances or flavoring agents, as standards like FEMA (US) do not endorse its broader application.
What are the regulatory and safety considerations for bornyl benzoate?
Regulatory evaluations, including those by entities such as FEMA (US), list bornyl benzoate for informational use only and do not recommend it for fragrance or flavor applications. Safety assessments have not identified specific hazards, and no precautionary labeling or hazard classifications have been assigned under OSHA or GHS frameworks. Toxicity data remain undetermined, so handling should follow standard chemical safety practices.

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

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Literature & References

[(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] benzoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6428443
Pubchem (sid):10544224
Flavornet:26927-90-2
Pherobase:View
Publications by PubMed
Contact and fumigant toxicity of Pinus densiflora needle hydrodistillate constituents and related compounds and efficacy of spray formulations containing the oil to Dermatophagoides farinae.
Antimicrobial activity of synthetic bornyl benzoates against Trypanosoma cruzi.
Synthesis, acute toxicity and anti-inflammatory effect of bornyl salicylate, a salicylic acid derivative.
Acaricidal activities of major constituents of essential oil of Juniperus chinensis leaves against house dust and stored food mites.
Fabrication and characterization of a novel inclusion complex of chiral monomer derived from (+)-camphor with beta-cyclodextrins.
Xanthine oxidase inhibitory activity of alkyl gallates.
Asymmetric methoxyselenenylations and cyclizations with 3-camphorseleno electrophiles containing oxime substituents at C-2. Formation of an unusual oxaselenazole from an oxime-substituted selenenyl bromide.
[Chemical constituents of fructus Amomi].
Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates.
Biosynthesis of monoterpenes: preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that Geranyl pyrophosphate is the preferred substrate for cyclization.

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
FooDB:FDB029760
ChemSpider:View

General Material Information

Preferred name bornyl benzoate
Trivial Name [(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] benzoate
Short Description borneol benzoate
Formula C17 H22 O2
CAS Number 26927-90-2
FDA UNII Search
Nikkaji Number J456.311E
NMR Predictor External link
Synonyms
  • borneol benzoate
  • [(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] benzoate

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 258.36074829102
Boiling Point 328 to 329°C @ 760 mm Hg
Vapor Pressure 0.000184 mmHg @ 25 °C
Flash Point TCC Value 149 °C TCC
logP (o/w) 5.365 est
Solubility
alcohol Yes
water, 0.6179 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Pine
pine, balsamic, herbal
Odor strength low
General comment At 100.00 %. pine balsam herbal

Potential Uses

Applications
Odor purposes Balsam , Herbal , Pine

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
Recommendation for bornyl benzoate usage levels up to:
not for fragrance use.
Recommendation for bornyl benzoate 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 :6428443
National Institute of Allergy and Infectious Diseases:Data
[(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] benzoate