(R)-(+)-Citronellal

Base Information

• Chemical Name: (R)-(+)-Citronellal
• CAS No.: 2385-77-5
• Deprecated CAS: 951036-03-6
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• Hs Code.: 2912190090
• European Community (EC) Number: 219-194-5
• DSSTox Substance ID: DTXSID6044482
• Nikkaji Number: J43.580E
• Wikidata: Q413787
• Metabolomics Workbench ID: 28006
• ChEMBL ID: CHEMBL1081721
• Mol file: 2385-77-5.mol

Synonyms:(R)-(+)-Citronellal;(+)-Citronellal;2385-77-5;(3R)-3,7-dimethyloct-6-enal;(R)-3,7-Dimethyloct-6-enal;(3R)-(+)-citronellal;(R)-citronellal;(3R)-3,7-Dimethyl-6-octenal;6-Octenal, 3,7-dimethyl-, (3R)-;(R)-3,7-dimethyl-6-octenal;CHEBI:299;EINECS 219-194-5;6-Octenal, 3,7-dimethyl-, (R)-;EC 219-194-5;Citronellol 96%;SCHEMBL457495;CHEMBL1081721;DTXSID6044482;3,7-Dimethyl-(3R)-6-Octenal;3,7-Dimethyl-6-octenal, (3R)-;MFCD00067089;AKOS025311453;CCG-214393;LMPR0102010007;6-Octenal, 3,7-dimethyl-, (theta)-;MS-22876;HY-111664;CS-0089462;(R)-(+)-Citronellal, technical grade, 90%;C09848;A901492;EN300-23312937;Q413787

Chemical Property of (R)-(+)-Citronellal

Chemical Property:

• Appearance/Colour: Colourless to slightly yellow liquid with intense lemon-citronella-rose aroma
• Vapor Pressure: 33.9Pa at 25℃
• Melting Point: 25°C
• Refractive Index: n20/D 1.448(lit.)
• Boiling Point: 208.4 °C at 760 mmHg
• Flash Point: 75.6 °C
• PSA: 17.07000
• Density: 0.835 g/cm³
• LogP: 2.95790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility.: 88mg/L
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

99.9% ^*data from raw suppliers

(+)-Citronellal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC=C(C)C)CC=O
• Isomeric SMILES: C[C@H](CCC=C(C)C)CC=O
• Uses: (+)-Citronellal is a monoterpene compound that is formed by the metabolism of plants. (+)-Citronellal is a natural insect repellant, and is the main component of citronellal oil. (+)-Citronellal is also used as a starting material in the one pot synthesis of (-)-Menthol (M218875).

Technology Process of (R)-(+)-Citronellal

There total 60 articles about (R)-(+)-Citronellal 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: 99.0%

cis-3,7-dimethyl-2,6-octadienal (106-26-3,96680-15-8) → (S)-Citronellal (5949-05-3) + (R)-Citronellal (2385-77-5)

Guidance literature:

With dicarbonyl(acetylacotonato)rhodium(I); carbon monoxide; (R,R)-chiraphos; hydrogen; iron; potassium hydroxide; at 20 - 60 ℃; for 21h; under 6000.6 Torr; Pressure; Temperature; Reagent/catalyst; Inert atmosphere; Autoclave;

Reference yield: 99.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → (S)-Citronellal (5949-05-3) + (R)-Citronellal (2385-77-5)

Guidance literature:

3,7-dimethyl-2,6-octadienal; With iron; potassium hydroxide; at 60 ℃; for 6h; under 37503.8 Torr;

With carbon monoxide; hydrogen; at 90 ℃; for 24h; under 3750.38 - 60006 Torr;

Reference yield: 56.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → (S)-Citronellal (5949-05-3) + (R)-Citronellal (2385-77-5) + Geraniol (106-24-1)

Guidance literature:

3,7-dimethyl-2,6-octadienal; With diethoxymethylane; Rh<(S,S)-Phebox>(OAc)2(aq); In toluene; at 30 ℃; for 1h;

With potassium fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; toluene; Further stages.;

DOI:10.1055/s-2006-951551

upstream raw materials:

(3R)-citronellol

aluminum isopropoxide

(E/Z)-3,7-dimethyl-2,6-octadienal

Geraniol

Downstream raw materials:

Isopulegol

(3R)-citronellol

4,8-dimethyl-7-nonen-2-ol

p-menthane-3,8-diol

Refernces

• 1、 Xie, Shengming,Wang, Bangjin,Zhang, Xinhuan,Zhang, Junhui,Zhang, Mei,Yuan, Liming. "Chiral 3D open-framework material Ni(D-cam)(H2O)2 used as GC stationary phase". . p. 27 - 32. Retrieved 2014.
• 2、 Tan, Zhuotao,Han, Yaoying,Fu, Yaping,Zhang, Xiaowang,Xu, Mengjiao,Na, Qi,Zhuang, Wei,Qu, Xudong,Ying, Hanjie,Zhu, Chenjie. "Investigating the Structure-Reactivity Relationships Between Nicotinamide Coenzyme Biomimetics and Pentaerythritol Tetranitrate Reductase". . p. 103 - 113. Retrieved 2021/10/07.
• 3、 Heindl, Sebastian,Lemmerer, Miran,Malzer, Nicolas,Matyasovsky, Ján,Maulide, Nuno,Riomet, Margaux. "Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO". supporting information. p. 19123 - 19127. Retrieved 2021/07/26.