dextro-borneol

Dextro-borneol is a bicyclic alcohol with a balsamic camphor odor, commonly used as a flavor and fragrance agent derived from natural essential oils.

General Material Description

Dextro-borneol is a bicyclic monoterpenoid alcohol with the molecular formula C₁₀H₁₈O. It appears as a solid with a characteristic balsamic and camphoraceous odor, contributing to its frequent use in fragrance and flavor formulations. Commonly referred to by synonyms such as d-Borneol and (+)-borneol, this compound belongs structurally to the bicyclo[2.2.1]heptan-2-ol family. It occurs naturally in various essential oils including camphor oil, lavender, rosemary, and nutmeg seed oil. The molecule’s stereochemistry is critical to its sensory characteristics and applications. Dextro-borneol is referenced in chemical databases such as ChEBI. Industrially, it is sourced primarily from natural extracts or may be synthesized for perfumery and flavoring purposes.

Occurrence, Applicability & Potential Uses

Dextro-borneol is naturally found in essential oils such as camphor oil, ginger rhizome oil, lavender, myristica fragrans (nutmeg) seed oil, olibanum, and rosemary. Its presence influences the characteristic balsamic, piney, and herbal odors associated with these plants. In commercial applications, dextro-borneol serves as a flavoring agent, especially in notes reminiscent of camphor tree bark, and contributes to fragrance compositions representing balsam, frankincense, lavender, pine, and spruce scents. The compound also finds use in formulations evoking herbal and fir aromas. Its usage levels are regulated under IFRA (International Fragrance Association) standards (Global), restricting dextro-borneol to a maximum of 2.0% concentration in fragrance concentrates to ensure safety.

Physico-Chemical Properties Summary

Dextro-borneol is a solid at room temperature, melting between 207 and 208°C at standard atmospheric pressure. It has a moderate vapor pressure of approximately 0.04 mmHg at 25°C, indicating low volatility relative to lighter fragrance constituents. The compound exhibits limited water solubility (approximately 740 mg/L at 25°C), yet it dissolves readily in alcohol and ether solvents, facilitating its formulation in various carrier systems. Its calculated logP of 2.85 reflects moderate hydrophobicity. The flash point, measured by the Tag Closed Cup method, is 150°F (~65.6°C), suggesting careful consideration in handling and storage. These physicochemical traits affect its olfactory release, blending compatibility, and stability within complex flavor and fragrance matrices.

FAQ

What is dextro-borneol and what are its primary uses?

Dextro-borneol is a stereoisomer of borneol, a bicyclic monoterpenoid alcohol characterized by a balsamic and camphor-like scent. It is primarily used as a flavoring and fragrance agent in perfumery and flavor industries. The compound imparts pine, herbal, and balsam nuances and is extracted from natural essential oils such as camphor oil and lavender. Its olfactory properties make it valuable in compositions requiring fresh, woody, or herbal notes.

Where does dextro-borneol naturally occur and how is it applied in industry?

Dextro-borneol naturally occurs in several essential oils including camphor oil, ginger rhizome oil, nutmeg seed oil, lavender, rosemary, and olibanum. Industrially, it is obtained from these botanical sources or synthesized for use. In flavor and fragrance applications, it is incorporated to enhance balsamic, pine, and herbal notes. Its solubility in alcohol and ether allows for flexible formulation in perfumes, personal care products, and flavor blends.

What regulations govern the use and safety of dextro-borneol in consumer products?

The International Fragrance Association (IFRA) regulates dextro-borneol usage globally, recommending maximum concentrations of 2.0% in fragrance concentrates to minimize potential risks. Safety data indicate it is harmful if swallowed, with standard precautions advising protective measures during handling. Toxicological evaluations and classification under European guidelines describe it as harmful (Xn), prompting adherence to safety data sheets and regulations such as REACH in Europe. Manufacturers reference regulatory bodies and material safety data to ensure compliant, safe application.

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
	(6S)-1,7,7-trimethylbicyclo[2.2.1]heptan-6-ol
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	439568
Pubchem (sid):	135058521

Publications by PubMed
Pharmacokinetics of natural borneol after oral administration in mice brain and its effect on excitation ratio.
[Determination of d-borneol in the different parts of Cinnamomum camphora by GC-MS].
[Stereochemical structure of d-borneol in "the Japanese Standards of Food Additives"].
Stomachic principles in ginger. III. An anti-ulcer principle, 6-gingesulfonic acid, and three monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, from Zingiberis Rhizoma originating in Taiwan.

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
CHEBI:	View
KEGG (GenomeNet):	C01765
HMDB (The Human Metabolome Database):	HMDB35818
FooDB:	FDB014580
Export Tariff Code:	2906.19.0000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: grades: technical.

General Material Information

Preferred name	dextro-borneol
Trivial Name	d-Borneol
Short Description	bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (2S)-
Formula	C10 H18 O
CAS Number	464-43-7
ECHA Number	207-352-6
FDA UNII	8D24LWT4FK
Nikkaji Number	J1.881.233I
Beilstein Number	2038056
MDL	MFCD00066427
NMR Predictor	External link
Synonyms	bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (2S)- (+)- borneol D- borneol (1R-endo)-1,7,7-trimethyl bicyclo(2.2.1)heptan-2-ol (2S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (6S)-1,7,7-trimethylbicyclo[2.2.1]heptan-6-ol (6S)-1,7,7-trimethylbicyclo[2.2.1]heptan-6-ol Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2S,4R)- Borneol, (1R,2S,4R)-(+)- Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R-endo)- (1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol d-Borneol (+)-(2S)-Borneol Borneol, (+)- (+)-Borneol (+)-endo-Borneol (1R)-(+)-Borneol d-(+)-Borneol (1R)-endo-Borneol (+)-2-Borneol Dexborneol (1R,2S,4R)-Borneol

Suppliers

Alfa Biotechnology	BOC Sciences
ExtraSynthese	Penta International
Santa Cruz Biotechnology	Sigma-Aldrich: Aldrich
Penta International Corporation

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	154.2526550293
Melting Point	207 to 208°C @ 760 mm Hg
Vapor Pressure	0.04 mmHg @ 25 °C
Flash Point TCC Value	65.56 °C TCC
logP (o/w)	2.85
Solubility
alcohol	Yes
ether	Yes
water, 740 mg/L @ 25 °C (exp)	Yes
water	No

Organoleptic Properties

Odor Type: Balsamic
pine, camphoreous, earthy
General comment	At 10.00 % in dipropylene glycol. pine camphor earthy

Occurrences

Potential Uses

Applications	flavor and fragrance agents
Odor purposes	Balsam , Camphor tree bark , Frankincense , Herbal , Lavender , Pine , Rosemary , Spruce
Flavoring purposes	Camphor tree bark
Other purposes	Fir

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed. S 02 - Keep out of the reach of children. S 22 - Do not breath dust. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.

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-rabbit LDLo 2000 mg/kg "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 204, 1989.
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-borneol usage levels up to:
	2.0000 % in the fragrance concentrate.