(+)-beta-Cedrene
[CAS# 546-28-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Decenone
• Name: (+)-beta-Cedrene
• Synonyms: (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.01,5]undecane
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• CAS Registry Number: 546-28-1
• EC Number: 208-898-8
• SMILES: C[C@@H]1CC[C@@H]2[C@]13CCC(=C)[C@H](C3)C2(C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.508, Calc.^*, 1.502
• Boiling Point: 263.1±7.0 °C (760 mmHg), Calc.^*, 263-264 °C
• Flash Point: 110.0±5.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08;GHS09 Danger
• Risk Statements: H304-H400-H410
• Safety Statements: P273-P301+P316-P331-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Aspiration hazard	Asp. Tox.	1	H304

Discovery and Applications

(+)-beta-Cedrene is a sesquiterpene hydrocarbon derived from the essential oils of cedarwood and various coniferous plants. Known for its distinctive woody and warm aroma, (+)-beta-Cedrene has a molecular formula of C₁₅H₂₄ and is classified under the isoprenoid family. Its discovery and isolation trace back to the late 19th and early 20th centuries when chemists first began characterizing essential oils and isolating individual components. Extracted through steam distillation or cold pressing from cedarwood oil, this compound was identified among other terpenes that contribute to cedarwood’s unique scent profile.

Structurally, (+)-beta-Cedrene is recognized by its bicyclic framework, which contributes to its stability and reactivity. The presence of a double bond in its structure gives it stereoisomeric forms, with (+)-beta-Cedrene referring to the specific enantiomer associated with its distinctive odor and bioactive properties. This compound's stereochemistry has been analyzed using techniques like gas chromatography and mass spectrometry, which have enabled the detailed study of its chemical characteristics and interactions. The substance’s stability and resistance to oxidation also make it suitable for long-lasting scent profiles in fragrance applications.

In the fragrance industry, (+)-beta-Cedrene is widely used as a component in perfumes and personal care products to evoke a natural, woody note. Its pleasant scent and stability make it an ideal ingredient in high-end and luxury fragrances, especially those intended to have a warm and earthy profile. This terpene also finds applications in scented products such as air fresheners and incense. Beyond its fragrance use, (+)-beta-Cedrene is valued in the flavor industry, where it is used sparingly in small quantities to add depth to certain flavor profiles.

Beyond its sensory applications, (+)-beta-Cedrene has shown potential in biological and pharmacological research. Studies have explored its possible anti-inflammatory, antimicrobial, and insect-repellent properties, which may be attributed to its interactions with cellular pathways in plants and insects. Due to its natural origins and low toxicity, it is also researched as an environmentally friendly insect repellent, offering an alternative to synthetic chemicals in pest control.

(+)-beta-Cedrene’s discovery and applications reflect its significant role in fragrance, flavoring, and natural product research. As studies continue to investigate its properties and potential uses, (+)-beta-Cedrene remains an essential compound, celebrated for its aromatic qualities and promising bioactive applications.

References

2022. Biomimetic Synthesis of Nor-Cedrene and Nor-Isozizaene Sesquiterpenoids and Exploration of Their Olfactive Properties. Chemistry (Weinheim an der Bergstrasse, Germany), 28(36).
DOI: 10.1002/chem.202201037

2018. α-Cedrene protects rodents from high-fat diet-induced adiposity via adenylyl cyclase 3. International Journal of Obesity, 43(1).
DOI: 10.1038/s41366-018-0176-0

2015. In vivo absorption and disposition of α-cedrene, a sesquiterpene constituent of cedarwood oil, in female and male rats. Drug Metabolism and Pharmacokinetics, 30(2).
DOI: 10.1016/j.dmpk.2014.12.003