Nerol

Base Information

• Chemical Name: Nerol
• CAS No.: 106-25-2
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2905.20
• European Community (EC) Number: 203-378-7
• UNII: 38G5P53250
• DSSTox Substance ID: DTXSID3026728
• Nikkaji Number: J3.241G
• Wikipedia: Nerol
• Wikidata: Q415359
• RXCUI: 2274605
• Metabolomics Workbench ID: 28009
• ChEMBL ID: CHEMBL452683
• Mol file: 106-25-2.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 Nerol

Chemical Property:

• Appearance/Colour: Clear colorless to almost colorless liquid
• Vapor Pressure: 0.0133mmHg at 25°C
• Melting Point: < -10oC
• Refractive Index: 1.475 - 1.476
• Boiling Point: 229.5 °C at 760 mmHg
• PKA: 14.45±0.10(Predicted)
• Flash Point: 76.7 °C
• PSA: 20.23000
• Density: 0.866 g/cm³
• LogP: 2.67140
• Storage Temp.: 2-8°C
• Solubility.: absolute ethanol: soluble(lit.)
• Water Solubility.: 1.311g/L(25 oC)
• 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:

99.9% ^*data from raw suppliers

Nerol ^*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:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=CCCC(=CCO)C)C
• Isomeric SMILES: CC(=CCC/C(=C\CO)/C)C
• Uses: The food flavors are mainly for the preparation of raspberry, strawberry and citrus fruit flavors and preparation of orange blossom, rose, magnolia main spices. It is a spice commonly used in jasmine, white flowers, lilac, lily of the valley, narcissus, carnation, mimosa, violet, vanilla, cymbidium, tuberose and citrus cologne. It is also commonly used in hyacinth, gardenia, osmanthus, acacia flavor formula. In the food flavor, its raspberry-strawberry flavor effect is commonly used. The product is also used in the preparation of daily makeup fragrance, such as violet, orange blossom, jasmine, lily of the valley, magnolia, cloves and other fragrance type makeup fragrance. It is widely used in orange blossom, rose, jasmine, tuberose and other fragrances of fragrant type and food flavor of raspberry, strawberry. It can also be used to produce ester spices. Nerol is a flavoring agent that is a colorless liquid with an odor resem- bling fresh, sweet roses and contains geranoils and other terpenic alcohols. it is miscible in alcohol, chloroform, and ether insoluble in water. it is obtained by synthesis. it is also termed cis-3,7-dime- thyl-2,6-octadien-1-ol. Nerol is an isomer of Geraniol (G367000), 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 aggregat ion. nerol is a primary alcohol used in perfumes, especially those with rose and orange blossom scents. nerol is a naturally occurring fraction in oil of lavender, orange leaf, palmarosa, rose, neroli, and petitgrain. It is colorless and has a rose-like scent.
• Description: Nerol has a fresh, sweet, rose-like odor and a bitter flavor. Nerol may be synthesized from pinene.

Technology Process of Nerol

There total 144 articles about Nerol 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: 82.0%

(Z)-3,7-dimethylocta-2,6-dien-1-yl benzoate (94417-89-7) → Nerol (106-25-2) + 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: 46.0%

2-methyl-3-buten-2-ol (115-18-4) → Nerol (106-25-2) + Geraniol (106-24-1) + (+/-)-lavandulol (58461-27-1,21090-68-6) + isoprene (78-79-5,9003-31-0)

Guidance literature:

With oxalic acid; In water; for 5h; Further byproducts given. Yields of byproduct given; Heating;

Reference yield: 8.0%

Geraniol (106-24-1) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + Nerol (106-25-2) + terpineol (98-55-5,2438-12-2)

Guidance literature:

With bis-trimethylsilanyl peroxide; bis(acetylacetonate)oxovanadium; In dichloromethane; at 25 ℃; for 7h;

DOI:10.1246/bcsj.58.844

upstream raw materials:

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

aluminum isopropoxide

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

Geraniol

Downstream raw materials:

cis-3,7-dimethyl-2,6-octadienal

3,7-dimethyl-2,6-octadienal

2,3,6,7-tetrabromo-3,7-dimethyl-octan-1-ol

glucuronic acid

Refernces

• 1、 Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.. "A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers". . p. 2198 - 2204. Retrieved 2004.
• 2、 Moiseenkov,A.M. et al.. "-". . p. 4759 - 4760. Retrieved 1979.
• 3、 Piva,Amougay,Pete. "Selective deprotection of diphenylmethylsilylethers of allylic and benzylic alcohols". . p. 219 - 226. Retrieved 1995.
• 4、 Selvam,Sonavane,Mohapatra,Jayaram. "Chemoselective reduction of α,β-unsaturated carbonyls over novel mesoporous CoHMA molecular sieves under hydrogen transfer conditions". . p. 542 - 544. Retrieved 2004.
• 5、 Pitzele et al.. "". . p. 269. Retrieved 1975.
• 6、 Schofield, Lee J.,Kerton, Owain J.,McMorn, Paul,Bethell, Donald,Ellwood, Simon,Hutchings, Graham J.. "Oxidation of α-hydroxy containing monoterpenes using titanium silicate catalysts: Comments on regioselectivity and the role of acidity". . p. 1475 - 1481. Retrieved 2002.
• 7、 -. "Method for preparing nerol from geraniol". Paragraph 0046-0047. . Retrieved 2021/01/25.
• 8、 -. "Improved method for preparation of nerol and geraniol and catalytic system thereof". Paragraph 0054-0055; 0058-0059. . Retrieved 2020/05/01.