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dextro-bornyl acetate

Dextro-bornyl acetate is a camphoraceous terpene ester with pine and herbal characteristics, found naturally in cedar and juniper woods.
Chemical Structure

General Material Description

Dextro-bornyl acetate is a bicyclic terpene acetate classified chemically as C12H20O2. It presents as a colorless to pale yellow liquid with a camphoraceous, pine needle, and herbal balsamic odor at 100% concentration. Known also under synonyms such as (+)-borneol acetate and (1R,2S,4R)-bornyl acetate, it is listed in chemical databases like ChEBI. This compound is primarily sourced from natural extracts of cedar and juniper species, contributing to their distinctive aromatic profiles. The ester functional group is formed from borneol and acetic acid, a factor influencing its sensory and chemical qualities.

Occurrence, Applicability & Potential Uses

Dextro-bornyl acetate occurs naturally in species such as cedar port, orford cedar, and Juniperus ashei Buchholz. It acts as an aromatic contributor in these woods, offering camphoraceous, herbal, and pine-like nuances. Although it is primarily known for its presence in essential oils, it is not used commercially for fragrance or flavor formulation. Regulatory frameworks, including REACH (Europe), have documented it mainly for informational purposes, confirming the absence of authorized flavor or fragrance applications.

Physico-Chemical Properties Summary

This compound exhibits a molecular weight of approximately 196.3 g/mol and a specific gravity close to 0.99 at 25°C, indicating near water-density behavior. Its boiling point ranges between 225 and 226°C at atmospheric pressure, while reduced pressure measurements show boiling near 92 to 93°C at 8 mm Hg. The flash point is estimated at 184°F (about 84°C). The estimated logP of 3.6 suggests moderate lipophilicity, contributing to limited water solubility but full solubility in alcohol solvents. Vapor pressure at 25°C is low (0.096 mmHg), signifying low volatility. These properties are important for understanding its behavior during extraction, storage, and potential formulation, although current uses exclude fragrance or flavor incorporation.

FAQ

What is dextro-bornyl acetate and where is it found?
Dextro-bornyl acetate is a natural terpene ester with the molecular formula C12H20O2. It features a camphoraceous, pine needle, and herbal aroma. This compound occurs naturally in various coniferous woods, notably cedar port orford cedar and Juniperus ashei Buchholz. It is responsible for contributing to the characteristic scent profiles of these plants.
How is dextro-bornyl acetate typically used and what are its properties?
While dextro-bornyl acetate possesses aromatic qualities including herbal and pine notes, it is categorized for information only and is not used in commercial fragrance or flavoring products. Physicochemically, it has a boiling point of about 225°C at 760 mm Hg, a flash point near 84°C, and moderate lipophilicity with a logP around 3.6. It dissolves well in alcohol but poorly in water, which informs handling and potential extraction processes.
Is dextro-bornyl acetate regulated or approved for consumer product use?
Dextro-bornyl acetate is not authorized for use in fragrances or flavors and carries an irritant classification in the European Union (Xi - Irritant), specifically denoted as irritating to eyes, respiratory system, and skin. Recommendations advise protective clothing when handling. Relevant regulatory references include REACH (EU) for classification and safety documentation. It is primarily of interest for chemical information rather than commercial formulation.

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Literature & References

[(3S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):443131
Pubchem (sid):135045938
Publications by PubMed
Essential-oil composition of the needles collected from natural populations of Macedonian pine (Pinus peuce Griseb.) from the Scardo-Pindic mountain system.
Chemical composition of essential oils of Grindelia squarrosa and G. hirsutula.
Chemical composition and free radical scavenging activity of the essential oil of Achillea ligustica growing wild in Lipari (Aeolian Islands, Sicily).
UV-B exposure of indoor-grown Picea abies seedlings causes an epigenetic effect and selective emission of terpenes.
Chemical composition of essential oil of Ferulago macrocarpa (Fenzl) Boiss. fruits.
Contact and fumigant toxicity of Pinus densiflora needle hydrodistillate constituents and related compounds and efficacy of spray formulations containing the oil to Dermatophagoides farinae.
Chemical composition and insecticidal activity of the essential oil of Illicium pachyphyllum fruits against two grain storage insects.
Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery.
Chemical markers in Origanum vulgare L. from Kumaon Himalayas: a chemosystematic study.
Analysis of essential oils from different organs of Scutellaria baicalensis.
Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum.
A new abietic acid-type diterpene glucoside from the needles of Pinus densiflora.
Acaricidal activities of major constituents of essential oil of Juniperus chinensis leaves against house dust and stored food mites.
Essential oil variability in natural populations of Picea omorika, a rare European conifer.
Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.
25 years of natural product R&D with New South Wales agriculture.
Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L.
Essential oil composition and antioxidant activity of aerial parts of Grindelia robusta from Central Italy.
Analysis by gas chromatography-mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss gathered in Nevakoh and Shahoo, Zagross mountain, West of Iran.
Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.
[Analysis of volatile constituents in leaves of three cypress species by gas chromatography/mass spectrometry].
Changes in anatomy and terpene chemistry in roots of Douglas-fir seedlings following treatment with methyl jasmonate.
The effect of selected monoterpenoids on the cellular slime mold, Dictyostelium discoideum NC4.
Total synthesis of dumsin. 1. Retrosynthetic strategy and the elaboration of key intermediates from (--)-bornyl acetate.
Incorporation of [1-(13)C]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum.
Foliar and cortex oleoresin variability of silver fir (Abies alba Mill.) in Albania.
Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality.
Variation in volatile compounds from tansy (Tanacetum vulgare L.) related to genetic and morphological differences of genotypes.
Decomposition of Terpenes by Ozone during Sampling on Tenax.
In vivo experimental model to evaluate the insect repellent N-N, diethylphenylacetamide in Periplaneta americana Linn.
A study on tansy chemotypes.

Other Information

General Material Information

Preferred name dextro-bornyl acetate
Trivial Name (+)-Borneol acetate
Short Description D-bornyl acetate
Formula C12 H20 O2
CAS Number 20347-65-3
ECHA Number 243-750-6
FDA UNII MN65CC8L89
Nikkaji Number J712.543G
Beilstein Number 1909308
MDL MFCD00135942
NMR Predictor External link
Synonyms
  • bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, exo-
  • (1R,2S,4R)- bornyl acetate
  • (1R,2S,4R)-(+)- bornyl acetate
  • D- bornyl acetate
  • [(3S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
  • [(3S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
  • Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, 2-acetate, (1R,2S,4R)-
  • Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R-endo)-
  • 2-Bornanol, acetate, (1R,2S,4R)-(+)-
  • Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R,2S,4R)-
  • Borneol, d-, acetate
  • d-Bornyl acetate
  • (+)-Bornyl, acetate
  • (+)-Borneol acetate

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 196.28979492188
Specific gravity @ 25 °C
Pounds per Gallon
Boiling Point 225 to 226°C @ 760 mm Hg
Boiling Point 92 to 93°C @ 8 mm Hg
Vapor Pressure 0.096 mmHg @ 25 °C
Flash Point TCC Value 84.4 °C TCC
logP (o/w) 3.602 est
Solubility
alcohol Yes
water, 9.721 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Camphoreous
fir needle, camphoreous, herbal, balsamic
General comment At 100.00 %. pine needle camphor herbal balsamic

Occurrences

Potential Uses

Applications
Odor purposes Herbal , Pine
Other purposes Fir

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
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:
information only not used for fragrances or flavors
Recommendation for dextro-bornyl acetate usage levels up to:
not for fragrance use.
Recommendation for dextro-bornyl acetate 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 :443131
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
[(3S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
Chemidplus:0020347653