10032-02-7

Basic information

• Product Name: GERANYL CAPROATE
• Synonyms: (2E)-3,7-Dimethyl-2,6-octadienyl hexanoate;(E)-3,7-Dimethylocta-2,6-dien-1-yl n-hexanoate;(e)-3,7-dimethylocta-2,6-dien-1-yln-hexanoate;2,6-Octadien-1-ol, 3,7-dimethyl-, hexanoate, (E)-;3,7-dimethyl-,hexanoate,(e)-6-octadien-1-ol;3,7-dimethyl-2,6-octadienylester,(e)-hexanoicaci;3,7-dimethylocta-2,6-dien-1-ylester,(e)-hexanoicaci;Geranyl hexanoate
• CAS NO: 10032-02-7
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.39
• EINECS: 233-102-0
• Product Categories: C15 to C19;Building Blocks;Chemical Synthesis;Ethers;New Products for Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 10032-02-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 335.57°C (rough estimate)
• Flash Point: 93℃
• Appearance: /
• Density: 0.892 g/mL at 25 °C
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: n20/D1.462
• CAS DataBase Reference: GERANYL CAPROATE(CAS DataBase Reference)
• NIST Chemistry Reference: GERANYL CAPROATE(10032-02-7)
• EPA Substance Registry System: GERANYL CAPROATE(10032-02-7)

Safety Data

• WGK Germany: 2
• RTECS: RG5926000
• Hazardous Substances Data: 10032-02-7(Hazardous Substances Data)

Usage

Description

Geranyl hexanoate has a rose-geranium odor with a strong undertone reminiscent of pineapple and banana.

Chemical Properties

Geranyl hexanoate has a rose-geranium odor with a strong undertone reminiscent of pineapple and banana.

Occurrence

Reported found in the essential oil of palmarosa and in the leaves of Phebalium dentatum Also reported found in pawpaw, purple passion fruit, kumquat peel oil and babaco fruit (Carica pentagona Heilborn)

Preparation

By an exchange reaction between methyl caproate and geraniol in the presence of a catalyst or sodium methylate.

InChI:InChI=1/C16H28O2/c1-5-6-7-11-16(17)18-13-12-15(4)10-8-9-14(2)3/h9,12H,5-8,10-11,13H2,1-4H3/b15-12+

Synthetic route

Geraniol (106-24-1) + 2,2'-bipyridyl-6-yl hexanoate (75178-10-8) → geraniol hexanoate (10032-02-7) + <2,2'-bipyridin>-6(1H)-one (101001-90-5)

Conditions	Yield
With cesium fluoride In acetonitrile for 7h; Heating;	A 88% B n/a

Geraniol (106-24-1) + Caproamide (628-02-4) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In n-heptane at 100℃; for 24h;	85%

Geraniol (106-24-1) + hexanoic acid (142-62-1) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With sodium hydroxide at 80℃; for 8h;	76.72%
In water at 30℃; for 18h; lipase from Penicillium cyclopium; Yield given;
With rapeseed lipase acetone powder In hexane at 40℃; for 48h; Enzymatic reaction;

Nerol (106-25-2) + n-hexanoic anhydride (2051-49-2) → geraniol hexanoate (10032-02-7) + (Z)-3,7-dimethyl-2,6-octadienyl ester hexanoic acid (68310-59-8)

Conditions	Yield
With lipase from hog pancreas In diethyl ether at 20℃; Product distribution; Rate constant; also with other lipases; other solvents;

Geraniol (106-24-1) + hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With Pseudomonas sp. lipase PS In hexane at 30℃; for 24h; also DL-citronellol and tributyrin; effect of enzyme load, concentration of reagents, addtion of water and pH; var. temp. and solvents;

Upstream product

• 106-24-1 Geraniol 
• 142-62-1 hexanoic acid 
• 621-70-5 hexanoic acid, 1,2,3-propanetriyl ester 
• 628-02-4 Caproamide 
• 75178-10-8 2,2'-bipyridyl-6-yl hexanoate 
• 106-25-2 Nerol 
• 2051-49-2 n-hexanoic anhydride 

Relevant articles and documents

STEREOSELECTIVE LIPASE-CATALYSED ACYLATION OF TERPENIC ALLYLIC ALCOHOLS BY FATTY ACID ANHYDRIDES

Lipase from pancreatic powder preferentially catalyses the acylation of the E isomer of terpenic allylic alcohols using fatty acid anhydrides as the acylating agent.The course of the reaction can be described by a first-order equation.

Lipase PS-catalyzed transesterification of citronellyl butyrate and geranyl caproate: Effect of reaction parameters

Pseudomonas sp. lipase PS was immobilized by adsorption and tested for its ability to catalyze the synthesis of citronellyl butyrate and geranyl caproate by transesterification in n-hexane. The reaction parameters investigated were: enzyme load, effect or

Scandium triflate catalyzed ester synthesis using primary amides

A scandium triflate (ScOTf)3 catalyzed methodology has been developed to synthesize esters from primary amides. Various primary and secondary aliphatic alcohols have been shown to react in n-heptane with a range of primary amides for 24 h.