Geraniol

Base Information

• Chemical Name: Geraniol
• CAS No.: 106-24-1
• Deprecated CAS: 8007-13-4,491611-08-6
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 29052900
• European Community (EC) Number: 203-377-1
• NSC Number: 46105,9279
• UNII: L837108USY
• DSSTox Substance ID: DTXSID8026727
• Nikkaji Number: J297.798B,J3.240I
• Wikipedia: Geraniol
• Wikidata: Q410836
• NCI Thesaurus Code: C63668
• RXCUI: 1368875
• Pharos Ligand ID: C59LZQWG7A27
• Metabolomics Workbench ID: 28015
• ChEMBL ID: CHEMBL25719
• Mol file: 106-24-1.mol

Synonyms:geraniol;geraniol, (E)-isomer;geraniol, (Z)-isomer;geraniol, 1-(14)C-labeled, (E)-isomer;geraniol, 2-(14)C-labeled, (E)-isomer;geraniol, titanium (4+) salt;nerol

Chemical Property of Geraniol

Chemical Property:

• Appearance/Colour: colourless to pale yellow liquid with an odour of roses
• Vapor Pressure: 0.013mmHg at 25°C
• Melting Point: -15 °C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 229.499 °C at 760 mmHg
• PKA: 14.45±0.10(Predicted)
• Flash Point: 76.667 °C
• PSA: 20.23000
• Density: 0.867 g/cm³
• LogP: 2.67140
• Storage Temp.: 2-8°C
• Solubility.: water: soluble0.1g/L at 25°C
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

Geraniol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC(=CCCC(=CCO)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CO)/C)C
• Description: Geraniol is a kind of monoterpenoid as well as alcohol. It is mainly existed in plant oils such as rose oil, palmarosa oil, and citronella oil. It can also be found in plants such as geraniums and lemongrass. It has a rose-like scent and is therefore used in perfumes as well as many kinds of flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, and blueberry. Another major application of geraniol is being used as an effective plant-based insect repellent for treatment of mosquitoes, house flies, stable flies, cockroaches, fire ants, fleas and lone star ticks. On the other hand, its scent can also attract bees. Geraniol has a characteristic rose-like odor. Geraniol may be prepared by fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene; commercial geraniol cannot be classified according to its alcohol content, as most of the recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol). Gas-chromatography techniques may be usefully employed to determine the geraniol content in a product.
• Uses: Geraniol is used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation. Geraniol was used in field evaluation of synthetic herbivore-induced plant volatiles as attractants to beneficial insects.It was used to evaluate the tumor-suppressive potency of isoprenoids in vitro and in vivo. geraniol is perfuming and with tonic properties. It is a primary constituent in many essential oils, including citronella, lavender, lemongrass, orange flower, and ylang-ylang.

Technology Process of Geraniol

There total 227 articles about Geraniol 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: 77.0%

(E)-geranyl benzoate (94-48-4) → Geraniol (106-24-1) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With 15-crown-5; (1-(2-(2,3-diisopropyl-1-methylguanidino)ethyl)-3-mesityl-1,3-dihydro-2H-imidazol-2-ylidene)copper(I) chloride; hydrogen; sodium t-butanolate; In 1,4-dioxane; at 60 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jacs.1c09626

Reference yield: 73.0%

(E)-1-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-2-methoxybenzene (1426824-93-2) → Geraniol (106-24-1) + 2-methylmethoxybenzene (578-58-5)

Guidance literature:

With N¹,N¹,N¹²,N¹²-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine; In N,N-dimethyl-formamide; for 72h; Inert atmosphere; Glovebox; UV-irradiation;

DOI:10.1002/anie.201208066

Reference yield: 64.0%

(E)-1-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-3,5-dimethoxybenzene (1426824-94-3) → Geraniol (106-24-1) + 1,3-dimethoxy-5-methylbenzene (4179-19-5)

Guidance literature:

With N¹,N¹,N¹²,N¹²-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine; In N,N-dimethyl-formamide; for 72h; Inert atmosphere; Glovebox; UV-irradiation;

DOI:10.1002/anie.201208066

upstream raw materials:

dichloro-acetic acid

2-methyl-3-buten-2-ol

7-methyl-3-methene-1,6-octadiene

linalool

Downstream raw materials:

4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene

trans-crotonic acid-(3,7-dimethyl-octa-2,6-dienyl ester)

Geranyl butyrate

geranyl formate

Refernces

• 1、 Nakano, Chiaki,Ootsuka, Takahiro,Takayama, Kazutoshi,Mitsui, Toshiaki,Sato, Tsutomu,Hoshino, Tsutomu. "Characterization of the Rv3378c gene product, a new diterpene synthasefor producing tuberculosinol and (13R, S)-isotuberculosinol (nosyberkol), from the mycobacterium tuberculosis H37Rv genome". . p. 75 - 81. Retrieved 2011.
• 2、 Zhang, Jingwen,Zhao, Jizhong,Wang, Li,Hu, Hongmei,Wang, Sheng,Yu, Ping,Wang, Rui. "Labeling of polyprenylated macromolecules using mild Ene reactions". . . Retrieved 2021.
• 3、 Mimoun. "Selective reduction of carbonyl compounds by polymethylhydrosiloxane in the presence of metal hydride catalysts". . p. 2582 - 2589. Retrieved 1999.
• 4、 Yoshimoto, Kazuya,Kawabata, Hirotoshi,Nakamichi, Natsuki,Hayashi, Masahiko. "Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): A novel catalyst for selective deacetylation". . p. 934 - 935. Retrieved 2001.
• 5、 Chou, Wayne K.W.,Ikeda, Haruo,Cane, David E.. "Cloning and characterization of Pfl-1841, a 2-methylenebornane synthase in Pseudomonas fluorescens PfO-1". . p. 6627 - 6632. Retrieved 2011.
• 6、 Ravikumar, K. S.,Baskaran, Sundarababu,Chandrasekaran, Srinivasan. "Diisopropoxytitanium(III) Tetrahydroborate: A Highly Useful Reagent for the Remarkably Selective 1,2-Reduction of α,β-Unsaturated Carbonyl Compounds". . p. 5981 - 5982. Retrieved 1993.
• 7、 Demissie, Zerihun A.,Erland, Lauren A.E.,Rheault, Mark R.,Mahmoud, Soheil S.. "The biosynthetic origin of irregular monoterpenes in lavandula: Isolation and biochemical characterization of a novel cis-prenyl diphosphate synthase gene, lavandulyl diphosphate synthase". . p. 6333 - 6341. Retrieved 2013.
• 8、 Brünig, Julian,Kirchner, Karl,Veiros, Luis F.,Weber, Stefan. "Manganese-Catalyzed Hydrogenation of Ketones under Mild and Base-free Conditions". . p. 1388 - 1394. Retrieved 2021.
• 9、 Julia, Marc,Verpeaux, Jean-Noel. "SYNTHESE A L'AIDE DE SULFONES-XXVI. SYNTHESE D'ALCOOLS ALLYLIQUES ET DE POLYPRENOLS PAR ATTACHEMENT D'UN SYNTHON PRENOL EN POSITION 4 E". . p. 3289 - 3292. Retrieved 1983.
• 10、 Magnard, Jean-Louis,Roccia, Aymeric,Caissard, Jean-Claude,Vergne, Philippe,Sun, Pulu,Hecquet, Romain,Dubois, Annick,Oyant, Laurence Hibrand-Saint,Jullien, Frédéric,Nicolè, Florence,Raymond, Olivier,Huguet, Stéphanie,Baltenweck, Raymonde,Meyer, Sophie,Claudel, Patricia,Jeauffre, Julien,Rohmer, Michel,Foucher, Fabrice,Hugueney, Philippe,Bendahmane, Mohammed,Baudino, Sylvie. "Biosynthesis of monoterpene scent compounds in roses". . p. 81 - 83. Retrieved 2015.