50894-66-1

Basic information

• Product Name: (+)-ALPHA-FUNEBRENE
• Synonyms: (+)-1,7-diepi-α-cedrene;(+)-α-funebrene;2,3,4,7,8,8aβ-Hexahydro-3β,6,8,8-tetramethyl-1H-3aβ,7β-methanoazulene;(+)-alpha-Funebrene >=95.0% (sum of enantiomers, GC)
• CAS NO: 50894-66-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.355
• Mol File: 50894-66-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 252 °C(lit.)
• Flash Point: 110.2°C
• Appearance: /
• Density: 0.925 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: n20/D 1.495
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-ALPHA-FUNEBRENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ALPHA-FUNEBRENE(50894-66-1)
• EPA Substance Registry System: (+)-ALPHA-FUNEBRENE(50894-66-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 50894-66-1(Hazardous Substances Data)

Usage

General Description

(+)-alpha-funebrene is a natural sesquiterpene alcohol and a constituent of various essential oils, including camphor oil and ginger oil. It is known for its pleasant, woody, and floral aroma, making it a popular ingredient in perfumes, soaps, and other cosmetic products. This chemical has also been studied for its potential antibacterial and antifungal properties, as well as its ability to repel insects. Additionally, (+)-alpha-funebrene is considered to have potential therapeutic benefits, such as anti-inflammatory and antioxidant properties, which may make it valuable in the development of pharmaceutical and nutraceutical products.

InChI:InChI=1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12-,13+,15-/m1/s1

Upstream product

• 77-53-2 α-cedrol 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 4683-24-3 1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 108-24-7 acetic anhydride 
• 59060-59-2 trans-ethyl 3,7-dimethyl-2-octenoate 
• 928-68-7 6-methylheptan-2-one 
• 1461-04-7 (2E)-3,7-dimethyl-2-octen-1-ol 
• 59060-54-7 (E)-1-bromo-3,7-dimethyloct-2-ene 
• 101726-06-1 6,10-Dimethylundeca-5-en-2-on 
• 17948-58-2 6,10-dimethylundec-5-en-2-one 
• 33778-05-1 ethyl (2E,6E)-3,7,11-trimethyldodeca-2,6-dienoate 
• 20576-56-1 (2E,6E)-10,11-dihydrofarnesol 
• 24163-98-2 3,7,11-trimethyl-2E,6Z,10-dodecatrienyl ethanoate 
• 4128-17-0 (2E,6E)-farnesyl acetate 

Downstream Products

• 13567-40-3 5-cedranone 
• 77-53-2 α-cedrol 
• 13567-42-5 5-Hydroxycedran 

Relevant articles and documents

Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ-Selinene and Mechanistic Studies

The synthesis of terpene natural products remains a challenging task due to the enormous structural diversity in this class of compounds. Synthetic catalysts are unable to reproduce the tail-to-head terpene cyclization of cyclase enzymes, which create this diversity from just a few simple linear terpene substrates. Recently, supramolecular structures have emerged as promising enzyme mimetics. In the present study, the hexameric resorcinarene capsule was utilized as an artificial cyclase to catalyze the cyclization of sesquiterpenes. With the cyclization reaction as the key step, the first total synthesis of the sesquiterpene natural product δ-selinene was achieved. This represents the first total synthesis of a sesquiterpene natural product that is based on the cyclization of a linear terpene precursor inside a supramolecular catalyst. To elucidate the reaction mechanism, detailed kinetic studies and kinetic isotope measurements were performed. Surprisingly, the obtained kinetic data indicated that a rate-limiting encapsulation step is operational in the cyclization of sesquiterpenes.

Total synthesis of α-cedrene: A new strategy utilizing N- aziridinylimine radical chemistry

Tandem free radical cycloaddition reaction of the N-Aziridinylimine intermediate produced tricyclo[5.3.1.01,5]undecane skeleton stereoselectively. A total synthesis of α-cedrene was completed in three step sequence from the cyclization product.

THE DIRECT CONVERSION OF EPOXIDES INTO ALKENES via IODOHYDRINS BY in situ GENERATED HI

Epoxides are easily converted into iodohydrins and alkenes are obtained from either epoxides or iodohydrins by treatment with HI, generated in situ from Ph3P*I2 in moist CH3CN.