762-29-8

Basic information

• Product Name: Farnesylacetone
• Synonyms: FARNESYLACETONE MIXTURE OF STEREO;5,9,13-Pentadecatriene-2-one, 6,10,14-trimethyl-;Pentadeca-5,9,13-triene-2-one, 6,10,14-trimethyl-;farnesylacetone, mixture of stereo isomers;6,10,14-trimethylpentadeca-5,9,13-trien-2-one;FARNESYLACETONE, MIXTURE OF ISOMERS, 97%;5,9,13-PENTADECATRIEN-2-ONE,6,10,14-TRIMETHYL-;6,10,-Trimethylpentadeca-5,9,-trien-2-on
• CAS NO: 762-29-8
• Molecular Formula: C₁₈H₃₀O
• Molecular Weight: 262.43
• EINECS: 212-097-9
• Product Categories: Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 762-29-8.mol

Chemical Properties

• Melting Point: 80.5-81.5 °C
• Boiling Point: 372.8 °C at 760 mmHg
• Flash Point: 110°C
• Appearance: Colourless or pale straw-coloured oily liquid; intensely sweet, floral odour
• Density: 0.88 g/mL at 20 °C(lit.)
• Vapor Pressure: 9.39E-06mmHg at 25°C
• Refractive Index: n20/D 1.481
• BRN: 1781239
• CAS DataBase Reference: Farnesylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Farnesylacetone(762-29-8)
• EPA Substance Registry System: Farnesylacetone(762-29-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 762-29-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Farnesylacetone is used as a precursor in the synthesis of various pharmaceutical compounds, particularly those related to the production of carotenoids. Its involvement in the biosynthesis process makes it a valuable component in the development of drugs and supplements that target specific health benefits associated with carotenoids.
Used in Cosmetic Industry:
In the cosmetic industry, farnesylacetone is utilized as a key ingredient in the formulation of products that aim to enhance skin health and appearance. Its role in carotenoid synthesis contributes to the development of cosmetics that promote skin protection, hydration, and rejuvenation.
Used in Nutraceutical Industry:
Farnesylacetone is employed as a vital component in the production of nutraceuticals, which are substances that provide additional health benefits beyond basic nutrition. Its presence in the synthesis of carotenoids allows for the creation of supplements and functional foods that support overall health and well-being.
Used in Agricultural Industry:
In agriculture, farnesylacetone plays a significant role in the enhancement of crop quality and yield. Its involvement in carotenoid biosynthesis can lead to the development of plant varieties with improved nutritional content, color, and resistance to various environmental stressors.
Overall, farnesylacetone's applications span across multiple industries, primarily due to its essential function in the biosynthesis of carotenoids. Its versatility and importance in various fields highlight its potential for further research and development in the future.

Preparation

By treating farnesyl bromide with sodium acetate, followed by treating with methanolic KOH.

InChI:InChI=1/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3/b16-11+,17-13-

Upstream product

• 7212-44-4 (+/-)-nerolidol 
• 141-97-9 ethyl acetoacetate 
• 40716-66-3 (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 
• 116-11-0 2-Methoxypropene 
• 53254-60-7 3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene 
• 59905-15-6 dehydronerolidol 
• 3796-70-1 trans geranyl acetone 
• 92747-33-6 methyl (E)-2-methyl-6-oxo-2-heptenyl carbonate 
• 112162-99-9 3-Oxo-butyric acid (E)-1,5,9-trimethyl-1-vinyl-deca-4,8-dienyl ester 
• 86948-99-4 (E)-7-(3,7-Dimethyl-octa-1,6-diene-3-sulfonyl)-6-methyl-hept-5-en-2-one 
• 22842-11-1 (5Ξ,9E)-6,10,14-trimethyl-pentadeca-5,9,13-trien-1-yne 
• 105-45-3 acetoacetic acid methyl ester 
• 4602-84-0 farnesol 
• 917-54-4 methyllithium 

Downstream Products

• 2387-69-1 3,7,11,15-tetramethyl-hexadeca-6,10,14-trien-1-yn-3-ol 
• 1027-71-0 sclareol oxide 
• 5153-92-4 sclareol oxide 
• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 1331771-17-5 (11E)-(4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl)benzene 
• 1182-68-9 2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4) 
• 6809-52-5 geranylgeranylacetone 
• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 68931-30-6 1,6,10,14-hexadecatetraen-3-ol, 3,7,11,15-tetramethyl- 
• 60437-17-4 3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenoic acid ethyl ester 

Relevant articles and documents

Method for synthesizing farnesyl acetone

The invention discloses a method for synthesizing farnesyl acetone. The method comprises the following steps of: mixing nerolidol and aluminum oxide, heating, dropwise adding methyl acetoacetate, carrying out heat preservation reaction after dropwise adding, evaporating generated methanol in the reaction process, and collecting generated carbon dioxide gas; and after finishing the reaction, filtering and separating aluminum oxide, and carrying out reduced pressure distillation on filtrate to collect the product farnesyl acetone. According to the method, the reaction yield is high, a catalyst can be separated through filtration and can be reused, washing of the reaction materials is avoided; waste water and waste containing metal ions are not generated, so that pollution to the environment is avoided; and generated by-products including methanol and carbon dioxide can be recycled.

NOVEL USE OF PHENYL PHOSPHINIC ACID

The present invention is directed towards a process for the manufacture of gamma, delta-unsaturated ketones of the general formula (III) by reacting a tertiary vinyl carbinol of the general formula (I) with an isopropenyl alkyl ether of the general formula (II) in the presence of a catalyst of the general formula (IV), wherein R1 and R6 are independently from each other methyl or ethyl, R3 is methyl, and R2 is a saturated or unsaturated linear, branched or cyclic hydrocarbyl group with 1 to 46 C atoms. The present invention is also directed towards the reaction mixture as such, i.e. the mixture of the compound of formula (I), the compound of formula (II) and the catalyst of formula (IV).

MANUFACTURE OF GAMMA-DELTA-UNSATURATED KETONES

A process for the manufacture of gamma-delta-unsaturated ketones of formula (R1)(R2)C = CH - CH2 - CH2 - CO - R3 (I), wherein R1 is methyl or ethyl; R2 is a saturated or unsaturated linear or cyclic hydrocarbon residue and R3 is methyl or ethyl, by reacting a tertiary vinyl carbinol of formula (R1)(R2)C(OH) - CH = CH2 (II) with an isopropenyl methyl or ethyl ether of formula H3C-C(OR3) = CH2 (III) in the presence of an ammonium salt as catalyst.

-SIGMATROPIC REARRANGEMENTS OF THE ACETOACETATES OF ALLYL ALCOHOLS (CARROLL REACTION) AND ALLYLPHENYL ETHERS (CLAISEN REACTION) ON THE SURFACE OF ADSORBENTS

A method has been developed for effecting rearrangements of allylacetoacetates to γ,δ-unsaturated ketones (Carroll rearrangement) and allylaryl ethers to the corresponding allylphenols (Claisen rearrangement) under conditions of adsorption on aluminum oxide and silica gel.The method provides a sharp reduction of the temperature of these reactions and improvement of their efficiency.

Allylic Carbonates. Efficient Allylating Agents of Carbonucleophiles in Palladium-Catalyzed Reactions under Neutral Conditions

Allylation of β-keto esters or malonates was carried out in good yields under neutral conditions by using allylic carbonates in the presence of palladium-phospine catalyst.Although simple ketones, esters, nitriles, and sulfones hardly react with allylic carbonates, α-alkenyl or α-aryl ketones, esters, nitriles, and sulfones were also allylated by using palladium-bis(diphenylphosphino)ethane catalyst under neutral conditions.

ORGANIC SYNTHESES WITH SULFONES (PART XXVIII) ;SYNTHESIS OF TERPENOID COMPOUNDS BY WAY OF MICHAEL ADDITION REACTIONS TO CONJUGATED DIENYL SULFONES.

Michael additions of ethanol and ketones to allyl-dienyl sulfones yielded di-allylic sulfones which were transformed into isoprenoid compounds by either Ramberg-Baecklund reaction or thermolysis.