alpha-Cedrene
[CAS# 469-61-4]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Decenone
• Name: alpha-Cedrene
• Synonyms: (1S,2R,5S)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undec-8-ene
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• CAS Registry Number: 469-61-4
• EC Number: 207-418-4
• SMILES: C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C

Properties

• Density: 0.932
• Boiling point: 261-262 °C
• Refractive index: 1.498
• alpha: -88 °(c=10%, EtOH)

Safety Data

• Hazard Symbols: GHS02;GHS08;GHS09 Danger
• Risk Statements: H226-H304-H400-H410
• Safety Statements: P210-P233-P240-P241-P242-P243-P273-P280-P301+P316-P303+P361+P353-P331-P370+P378-P391-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Aspiration hazard	Asp. Tox.	1	H304
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Alpha-Cedrene is found in essential oils extracted from cedarwood, particularly from species such as Atlantic cedarwood and Virginia juniper. This sesquiterpene is responsible for the distinctive woody and resinous aroma of cedarwood oil. Its discovery dates back to early studies of plant essential oils, when researchers isolated and identified its chemical structure. Alpha-Cedrene is characterized by a molecular structure consisting of three isoprene units. It has a chemical formula of C15H24, a double ring structure, and a molecular weight of approximately 204.35 g/mol. The compound is lipophilic, meaning it dissolves easily in fats and oils, enhancing its usefulness in a variety of applications.

Alpha-Cedrene is prized for its pleasant aroma, reminiscent of cedarwood. It is a key ingredient in perfumes, colognes, and other fragrance products that give off a warm, woody scent. In cosmetics, it is used in skincare products, soaps, and shampoos for its natural scent and potential skin-soothing properties.

In pharmaceuticals, alpha-Cedrene is studied for its potential therapeutic benefits. Studies have shown that it has anti-inflammatory and antimicrobial properties, making it a candidate for formulations to treat skin conditions and topical infections. Its natural origin and recognized safety profile make it attractive in alternative medicine practices.

α-Cedrene has insecticidal properties, specifically targeting mosquitoes and other pests. This property makes it an important ingredient in insect repellents, household sprays, and agricultural formulations designed to deter or eliminate pests without the use of synthetic chemicals.

The natural origin of α-Cedrene is in line with the growing consumer preference for environmentally friendly and sustainable products. However, its concentrated form can pose risks if not handled properly, so safety guidelines must be followed in manufacturing and application. Environmental impact studies are currently underway to assess its biodegradability and potential impact on ecosystems.

References

2017. Olfactory receptor 10J5 responding to alpha-cedrene regulates hepatic steatosis via the cAMP-PKA pathway. Scientific Reports, 7.
DOI: 10.1038/s41598-017-10379-x

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

2016. The Wender cedrene synthesis revisited: A catalytic enantioselective entry to the chiral key intermediate. Synthesis, 48.
DOI: 10.1055/s-0036-1588602