512-13-0

Basic information

• Product Name: FENCHOL
• Synonyms: FEMA 2480;(1R)-ENDO-(+)-FENCHYL ALCOHOL;(1R)-ENDO-(+)-FENCHOL;ALPHA FENCHOL;alpha-Fenchyl alcohol;endo-alpha-Fenchol;Endo-fenchol;(1S-endo)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS NO: 512-13-0
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 216-639-5
• Mol File: 512-13-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 43-46 °C
• Boiling Point: 201-202 °C(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 0.9034
• Refractive Index: 1.4702 (estimate)
• PKA: 15.38±0.60(Predicted)
• CAS DataBase Reference: FENCHOL(CAS DataBase Reference)
• NIST Chemistry Reference: FENCHOL(512-13-0)
• EPA Substance Registry System: FENCHOL(512-13-0)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 512-13-0(Hazardous Substances Data)

Usage

Description

FENCHOL, also known as 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol, is a fenchane monoterpenoid with a unique structure characterized by a bicyclo[2.2.1]heptane ring substituted by methyl groups at positions 1, 3, and 3, and a hydroxy group at position 2 (the 1S,2S,4R stereoisomer). This organic compound is derived from natural sources and exhibits various properties that make it useful in different applications.

Uses

Used in the Flavor and Fragrance Industry:
FENCHOL is used as a key ingredient in the flavor and fragrance industry for its distinctive camphoraceous and piney odor. It is widely utilized in the creation of perfumes, colognes, and other scented products due to its ability to provide a fresh, clean, and slightly woody aroma.
Used in the Pharmaceutical Industry:
FENCHOL is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs, particularly those targeting the central nervous system and other therapeutic areas.
Used in the Chemical Industry:
FENCHOL is used as a starting material for the production of various chemicals, including insect repellents, biodegradable polymers, and other specialty chemicals. Its unique structure and reactivity make it a valuable component in the synthesis of these materials.
Used in the Cosmetic Industry:
FENCHOL is used as a component in the formulation of cosmetics, such as lotions, creams, and shampoos, due to its pleasant scent and potential antimicrobial properties. It can also be used as a fixative to help extend the longevity of fragrances in cosmetic products.

InChI:InChI=1/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7?,8?,10-/m0/s1

Upstream product

• 1195-79-5 1,3,3-trimethyl-2-norbornanone 
• 7785-26-4 (-)-α-pinene 
• 108-24-7 acetic anhydride 
• 60-29-7 diethyl ether 
• 124-38-9 carbon dioxide 
• 4695-62-9 fenchone 
• 6248-94-8 (+)-2-hydroxy-1,3,3-trimethyl-norbornane-2-carboxylic acid 
• 80-56-8 Pinene 
• 80-26-2 terpinyl acetate 
• 108-88-3 toluene 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 486-25-9 9-fluorenone 
• 1689-64-1 9-Fluorenol 

Downstream Products

• 126823-64-1 N-<(o-nitrophenyl)sulfenyl>-β-2-thienyl-D,L-alanine (+)-β-fenchyl ester 
• 1195-79-5 1,3,3-trimethyl-2-norbornanone 
• 6248-88-0 β-Fenchen 
• 488-97-1 cyclofenchene 
• 4695-62-9 fenchone 
• 470-08-6 (-)-β-fenchol 
• 13851-11-1 α-fenchyl acetate 
• 103300-55-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 
• 103300-55-6 (S)-3-Benzyloxycarbonylamino-N-[phenyl-((1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid benzyl ester 
• 103366-56-9 L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 
• 103300-60-3 (S)-3-Amino-N-[phenyl-((1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid 
• 103300-54-5 D-phenylglycine (-)-α-fenchyl ester 
• 103300-54-5 Amino-phenyl-acetic acid (1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 124442-03-1 (S)-3-Benzyloxycarbonylamino-N-[(2-fluoro-phenyl)-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid benzyl ester 

Relevant articles and documents

Synthesis of Terpineol from Alpha-Pinene Catalyzed by α-Hydroxy Acids

We report the use of five alpha-hydroxy acids (citric, tartaric, mandelic, lactic and glycolic acids) as catalysts in the synthesis of terpineol from alpha-pinene. The study found that the hydration rate of pinene was slow when only catalyzed by alpha-hydroxyl acids. Ternary composite catalysts, composed of AHAs, phosphoric acid, and acetic acid, had a good catalytic performance. The reaction step was hydrolysis of the intermediate terpinyl acetate, which yielded terpineol. The optimal reaction conditions were as follows: alpha-pinene, acetic acid, water, citric acid, and phosphoric acid, at a mass ratio of 1:2.5:1:(0.1–0.05):0.05, a reaction temperature of 70? C, and a reaction time of 12–15 h. The conversion of alpha-pinene was 96%, the content of alpha-terpineol was 46.9%, and the selectivity of alpha-terpineol was 48.1%. In addition, the catalytic performance of monolayer graphene oxide and its composite catalyst with citric acid was studied, with acetic acid used as an additive.

Synthesis and sweetness characteristics of L-aspartyl-D-alanine fenchyl esters

Four isomers of the L-aspartyl-D-alanine fenchyl esters were prepared as potential peptide sweeteners. L-Aspartyl-D-alanine (+)-α-fenchyl ester and L-aspartyl-D-alanine (-)-β-fenchyl ester showed sweetness with potencies 250 and 160 times higher than that of sucrose, respectively. In contrast, L-aspartyl-D-alanine (+)-β-fenchyl ester and L-aspartyl-D-alanine (-)-α-fenchyl ester had the highest sweetness potencies at 5700 and 1100 times that of sucrose, respectively. In particular, L-aspartyl-D-alanine (-)-α-fenchyl ester had an excellent sweetness quality, but L-aspartyl-D-alanine (+)-β-fenchyl ester did not have an excellent quality of sweetness because it displayed an aftertaste caused by the strong sweetness.

High potency dipeptide sweeteners. 1. L-aspartyl-D-phenylglycine esters

Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxyphenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-α- and (+)-β-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.