51411-24-6

Basic information

• Product Name: (+/-)DIHYDRAFARNESOL
• Synonyms: (+/-)DIHYDRAFARNESOL;2,3-Dihydrofarnesol;3,7,11-Trimethyl-6,10-dodecadien-1-ol;(E)-3,7,11-Trimethyl-6,10-dodecadien-1-ol;(+/-)-DIHYDROFARNESOL
• CAS NO: 51411-24-6
• Molecular Formula: C₁₅H₂₈O
• Molecular Weight: 224.38
• Mol File: 51411-24-6.mol

Chemical Properties

• Boiling Point: 307.8°C at 760 mmHg
• Flash Point: 104.9°C
• Appearance: /
• Density: 0.86g/cm³
• Vapor Pressure: 6.5E-05mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.12±0.10(Predicted)
• CAS DataBase Reference: (+/-)DIHYDRAFARNESOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)DIHYDRAFARNESOL(51411-24-6)
• EPA Substance Registry System: (+/-)DIHYDRAFARNESOL(51411-24-6)

Safety Data

• Hazardous Substances Data: 51411-24-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)DIHYDRAFARNESOL is used as an antimicrobial agent for inhibiting the growth of dermatophytes, which are fungi that cause skin, hair, and nail infections. Its ability to suppress the growth of these fungi makes it a valuable component in the development of treatments for dermatophytosis and other related conditions.
Used in Perfumery:
(+/-)DIHYDRAFARNESOL is used as a fragrance ingredient for its characteristic lily-of-the-valley odor. This application takes advantage of the compound's unique scent, which can be used to create a wide range of perfumes and fragrances for various products, including cosmetics, personal care items, and household products.
Used in Food and Beverage Industry:
(+/-)DIHYDRAFARNESOL is used as a flavoring agent in the food and beverage industry, particularly in the production of tequila. Its distinct metallic and balsamic side note, along with its lily-of-the-valley odor, contribute to the overall taste and aroma profile of the final product.
Used in Marine Biology Research:
(+/-)DIHYDRAFARNESOL is used as a chemical marker in marine biology research, particularly in the study of marine brown and red algae. The presence of (+/-)DIHYDRAFARNESOL in these organisms can provide valuable insights into their ecological roles, biochemistry, and potential applications in various fields, such as biotechnology and pharmaceuticals.

Preparation

Prepared in a patented process by selectively hydrogenating farnesol in the presence of a catalyst.

InChI:InChI=1/C15H28O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,15-16H,5-6,8,10-12H2,1-4H3

Upstream product

• 72019-02-4 (6E)-3,7,11-trimethyldodeca-2,6,10-trienal 
• 106-28-5 Farnesol 
• 34114-96-0 methyl (S,E)-2,3-dihydrofarnesenoate 
• 3899-18-1 (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene 
• 40716-66-3 (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 
• 172376-82-8 (R)-2,3-dihydrofarnesal 
• 18794-84-8 (E)-β-farnesene 
• 1574173-72-0 (1E,3R,6E)-N,N-diethyl-3,7,11-trimethyldodeca-1,6,10-trien-1-amine 
• 3482-62-0 N,N-diethyl-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]amine 
• 69097-01-4 (R)-4-bromo-3-methylbut-1-ene 
• 6138-90-5 trans-geranyl bromide 
• 55759-32-5 (S)-dihydrofarnesene 
• 61733-49-1 methyl (R)-3-(E)-6-2,3-dihydrofarnesoate 
• 41494-94-4 (6E)-3,7,11-trimethyl-1,2,6,10-dodecatetraen-1-yl acetate 

Downstream Products

• 76164-07-3 2,3-dihydro-6(Z)-farnesyl tosylate 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 194934-66-2 (3S)-dihydrofarnesal 
• 34114-96-0 methyl (S,E)-2,3-dihydrofarnesenoate 
• 298713-15-2 (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione 
• 298713-13-0 (3S,10S,6E)-12-benzenesulfinyl-10-isopropyl-3,7-dimethyl-dodec-6-ene-1,11-diol 
• 298713-14-1 (3S,10S,6E)-12-benzenesulfinyl-10-isopropyl-3,7-dimethyl-11-oxo-dodec-6-enal 
• 172376-82-8 (R)-2,3-dihydrofarnesal 
• 76164-14-2 dihydro-α-bisabolene 
• 76164-13-1 dihydro-β-bisabolene 

Relevant articles and documents

Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry

The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a species-specific manner for semiochemical formation.

Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs

Some amphibians use chemical signals in addition to optical and acoustical signals to transmit information. Males of mantellid frogs from Madagascar and hyperoliid frogs from Africa emit complex, species- and sex-specific bouquets of volatiles from their femoral or gular glands. We report here on the identification, synthesis, and determination of the absolute configuration of a macrocyclic lactone occurring in several species of both families, (S)-3,7,11-dodec-6,10-dien-12-olide (S-14, frogolide). Macrolides are a preferred compound class of frog volatiles. Nevertheless, frogolide is the first macrocyclic lactone obviously derived from the terpene pathway, in contrast to known frog macrolides that are usually formed via the fatty acid biosynthetic pathway.

Preparation of regio- and stereoisomeric di- and tetrahydrogeranylgeraniols and identification of esterifying groups in natural (bacterio)chlorophylls

All regioisomeric di- and tetrahydrogeranylgeraniols possessing the C2[dbnd]C3 double bond were prepared as authentic samples. The synthetic C20-isoprenoid alcohols were separated well by gas chromatography. Based on the chromatographic analysis, the enzymatic reduction pathway of a geranylgeranyl group was investigated to identify the last stage of (bacterio)chlorophyll biosynthesis in phototrophs. The geranylgeranyl group was triply reduced to the phytyl group through the first regio- and stereospecific hydrogenation of C10[dbnd]C11 to C10H–C11(S)H, the second of C6[dbnd]C7 to C6H–C7(S)H, and the third of C14[dbnd]C15 to C14H–C15H. The identification of the reduction sequence completes the biosynthetic pathways for naturally occurring chlorophyll-a and bacteriochlorophyll-a bearing a phytyl group as the esterifying moiety in the 17-propionate residues.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL

PROBLEM TO BE SOLVED: To provide a synthetic intermediate useful for obtaining optically active 2,3-dihydrofarnesal high in chemical purity and optical purity, and a satisfactorily efficient method for producing the intermediate. SOLUTION: Provided is optically active farnesyl enamine represented by formula (4) (*denotes an asymmetric carbon atom; R1 and R2 respectively independently denote H, a substituted/unsubstituted 1-20C alkyl group, a substituted/unsubstituted 3-8 membered-ring alicyclic group, a substituted/unsubstituted 6-15C aryl group; a substituted/unsubstituted 2-15C heterocyclic group or a substituted/unsubstituted 7-12C aralkyl group; and R1 and R2 are not simultaneously H or R1 and R2 may be coupled to form a ring). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

FRAGRANCE COMPOSITION

The present invention relates to: a fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass% or more and an optical purity of 50% e.e. or more; a cosmetic product containing the fragrance composition; and a method for improving an aroma using the fragrance composition.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL

A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:

METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL

A method for producing an optically active 2,3-dihydrofarnesal represented by formula (1): the method comprising: subjecting β-farnesene represented by formula (2) to amination in the presence of a lithium salt of an amine: to obtain (2E)-farnesyl allylamine represented by general formula (3): subsequently subjecting to asymmetric isomerization to obtain an optically active farnesyl enamine represented by general formula (4): and subjecting the optically active farnesyl enamine to solvolysis, wherein R1, R2, and * are as defined in claims of the present application.

Enantioselective access to (-)-Ambrox starting from β-farnesene

Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t

Ruthenium-catalyzed asymmetric transfer hydrogenation of allylic alcohols by an enantioselective isomerization/transfer hydrogenation mechanism

Reducing hazards: A asymmetric transfer hydrogen reaction was developed to reduce prochiral allylic alcohols in high yield and excellent enantioselectivity (see example). Mechanistic studies indicate a novel enantioselective isomerization/transfer hydrogenation mechanism. This new reaction is much safer than high-pressure hydrogenation using H2 gas. Copyright

Enantio- and diastereoselective hydrogenation of farnesol and O-protected derivatives: Stereocontrol by changing the C=C bond configuration

(Chemical Presented) Four isomers-one catalyst: The four stereoisomers of hexahydrofarnesol can be prepared with high enantio- and diastereoselectivity by using the same chiral iridium catalyst 1 with different cis/trans isomers of farnesol (see scheme; B