Geranyl acetate

Base Information

• Chemical Name: Geranyl acetate
• CAS No.: 105-87-3
• Deprecated CAS: 130396-84-8,8022-83-1,8022-83-1
• Molecular Formula: C12H20O2
• Molecular Weight: 196.29
• Hs Code.: 29153900
• European Community (EC) Number: 203-341-5
• NSC Number: 2584
• UNII: 3W81YG7P9R
• DSSTox Substance ID: DTXSID0020654
• Nikkaji Number: J4.032K,J46.477E
• Wikipedia: Geranyl_acetate
• Wikidata: Q426437
• RXCUI: 1807120
• Metabolomics Workbench ID: 3834
• ChEMBL ID: CHEMBL1369384
• Mol file: 105-87-3.mol

Synonyms:geraniol acetate;geraniol acetate, (E)-isomer;geraniol acetate, (Z)-isomer;geranyl acetate;nerol acetate;neryl acetate

Chemical Property of Geranyl acetate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.0256mmHg at 25°C
• Melting Point: < 25 °C
• Refractive Index: n20/D 1.462
• Boiling Point: 247.5 °C at 760 mmHg
• Flash Point: 98.9 °C
• PSA: 26.30000
• Density: 0.904 g/cm³
• LogP: 3.24220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

β-GeranylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(=CCCC(=CCOC(=O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COC(=O)C)/C)C
• Description: Geranyl acetate, used in numerous essential oils, is one of the most important natural fragrances. It is a colorless organic liquid with a sweet fruity or citrus top-note aroma. It can be used in soaps, creams, and in food as a fragrant and flavoring agent, in over 60 flavors including rose, lavender, carrot, lemongrass, peach, citronella, and many more. It is a major constituent of lime oil, with great economic importance. In addition, its antifungal, anti-inflammatory, and antimicrobial effects have been investigated. It has been found safe for food use by the FDA. Geranyl acetate is a monoterpene that has been found in C. sativa with diverse biological activities. It reduces compound action potential (CAP) peak amplitude in isolated frog sciatic nerves (IC50 = 0.51 mM). Geranyl acetate inhibits the radial growth of M. gypsum, T. vercossum, and C. tropicalis on solid media. It is sporicidal against B. subtilis when used at a concentration of 1% in an agar diffusion assay. Geranyl acetate inhibits growth of COLO 205 cells (IC50 = 30 μM) via induction of DNA damage, cell cycle arrest at the G2/M phase, and mitochondrial apoptosis. Geranyl acetate has a pleasant, flowery odor reminiscent of rose lavender. It has a burning taste, initially somewhat bitter and then sweet. It is produced from geraniol by acetylation or by fractional distillation of essential oils in which it is present.
• Uses: β-Geranyl Acetate is found in essential oils such as Moroccan commercial essential oils which has anti-oxidant, anti-inflammatory and anti-proliferative activities; and in Salvia scabiosifolia from Bulgaria. Perfumery, flavoring

Technology Process of Geranyl acetate

There total 73 articles about Geranyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Geraniol (106-24-1) + acetic anhydride (108-24-7) → 3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1)

Guidance literature:

With pyridine; Ambient temperature;

Reference yield: 100.0%

vinyl acetate (108-05-4,9003-20-7) + Geraniol (106-24-1) → 3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1)

Guidance literature:

With dilithium tetra(tert-butyl)zincate; In toluene; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.03.096

Reference yield: 99.9%

Geraniol (106-24-1) + acetic acid (64-19-7,77671-22-8) → 3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1)

Guidance literature:

With Candida antarctica lipase B; at 50 ℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;

DOI:10.1039/c2gc36081k

upstream raw materials:

geranyl bromide

sodium acetate

3,7-dimethylocta-1,6-dien-3-ol

acetic anhydride

Downstream raw materials:

2-r-acetoxymethyl-1,3,3-trimethyl-4-t-(4-hydroxy-3-methyl-2-E-buten-1-yl)-1-t-cyclohexanol

2-r-acetoxymethyl-1,3,3-trimethyl-4-c-(4-hydroxy-3-methyl-2-E-buten-1-yl)-1-t-cyclohexanol

acetate de dimethyl-3,7 methoxy-7 phenylseleno-6 octene-2 yle

Acetic acid (E)-7-methoxy-3,7-dimethyl-6-phenylselanyl-oct-2-enyl ester

Refernces

• 1、 Inoue, Yoshihisa,Goan, Kazuyoshi,Hakushi, Tadao. "Vakuum UV Photolyses of Some Bichromophoric Alkenes Possesing Hydroxyl or Methoxycarbonyl Group". . p. 2217 - 2220. Retrieved 1985.
• 2、 Chandrasekhar,Ramachandar,Reddy, M. Venkat,Takhi, Mohamed. "A single step conversion of tetrahydropyranyl ethers to acetates". . p. 4729 - 4731. Retrieved 2000.
• 3、 Dawson, Glenn W.,Pickett, John A.,Smiley, Diane W. M.. "The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways". . p. 351 - 361. Retrieved 1996.
• 4、 Chatterjee,Bhattacharyya. "Synthesis of monoterpene esters by alcoholysis reaction with Mucor miehei lipase in a solvent-free system". . p. 651 - 655. Retrieved 1998.
• 5、 Nishida, Takanori,Matsuda, Daiki,Kasuga, Issei,Orita, Akihiro,Otera, Junzo. "A simple method for the removal of organotin residues from acetates and a homoallylic alcohol prepared from organostannane reagents: Column chromatography using 10%-moist SiO2". . p. 1280 - 1282. Retrieved 2016.
• 6、 Suhara, Yoshitomo,Murakami, Aya,Kamao, Maya,Mimatsu, Shino,Nakagawa, Kimie,Tsugawa, Naoko,Okano, Toshio. "Efficient synthesis and biological evaluation of ω-oxygenated analogues of vitamin K2: Study of modification and structure-activity relationship of vitamin K2 metabolites". . p. 1622 - 1625. Retrieved 2007.
• 7、 Coates,Melvin jr.. "". . p. 865. Retrieved 1970.
• 8、 Badgujar, Kirtikumar C.,Bhanage, Bhalchandra M.. "Synthesis of geranyl acetate in non-aqueous media using immobilized Pseudomonas cepacia lipase on biodegradable polymer film: Kinetic modelling and chain length effect study". . p. 1304 - 1313. Retrieved 2014.
• 9、 Costa, Vinicius V.,Da Silva Rocha, Kelly A.,Oliveira, Luiz C. A.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.,Gusevskaya, Elena V.. "Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: Acetylation of nopol and terpenic alcohols". . p. 43217 - 43222. Retrieved 2016.
• 10、 Yee,Akoh. "Enzymatic synthesis of geranyl acetate by transesterification with acetic anhydride as acyl donor". . p. 1379 - 1384. Retrieved 1996.