Linalool

Base Information

• Chemical Name: Linalool
• CAS No.: 78-70-6
• Deprecated CAS: 11024-20-7,22564-99-4,22564-99-4
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2905.29
• European Community (EC) Number: 201-134-4,245-083-6
• ICSC Number: 0912
• NSC Number: 3789
• UNII: D81QY6I88E
• DSSTox Substance ID: DTXSID7025502
• Nikkaji Number: J2.830D,J86.711J
• Wikipedia: Linalool
• Wikidata: Q410932
• RXCUI: 1368896
• Pharos Ligand ID: 1NY1L4K66J13
• Metabolomics Workbench ID: 129614
• ChEMBL ID: CHEMBL25306
• Mol file: 78-70-6.mol

Synonyms:3,7-dimethyl-1,6-octadien-3-ol;7-methyl-3-methyleneocta-4,6-dien-2-ol;allo-ocimenol;linalool;linalool, (+-)-isomer;linalool, (R)-isomer;linalool, (S)-isomer;linalool, titanium (4+) salt;muguol

Chemical Property of Linalool

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.17 mm Hg ( 25 °C)
• Melting Point: 25°C
• Refractive Index: 1.460 - 1.465
• Boiling Point: 198.5 °C at 760 mmHg
• PKA: 14.51±0.29(Predicted)
• Flash Point: 84.9 °C
• PSA: 20.23000
• Density: 0.859 g/cm³
• LogP: 2.66980
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble1ml/4ml, clear, colorless (60% ethanol)
• Water Solubility.: 1.45 g/L (25 ºC)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

95%, 99% ^*data from raw suppliers

Linalool ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=CCCC(C)(C=C)O)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin.
• Effects of Long Term Exposure: The substance may have effects on the liver.
• Uses: 1. It is used for the preparation of cosmetics, soaps, detergents, food and other flavors. 2. GB 276011996 states it is classified into food flavor allowed for temporary use. It is mainly used for the preparation of flavors or aromatic seasoning of pineapple, peach, and chocolate. 3. It is widely presented in flowers, fruits, stems, leaves, roots and green Rosa Chinensis viridiflora. It has a wide range of application, not only for all the floral flavors, such as sweet bean curd, jasmine, Convallaria majalis, lilac, etc., it can also be applied in fruit flavor type, Fen-flavor type, wood flavor type, aldehyde flavor type, oriental flavor type, amber scent type, chypre type, fern-type and other non-flower type of flavor. It can also be used in formulating orange leaf, bergamot, lavender, and some kinds of artificial oils such as hybrid lavender oil. It is mostly used in soap or flavor. It can be used for food flavor. 4. Linalool is a kind of important spices and is the blending raw materials for producing various kinds of artificial oil, also used extensively for the manufacturing of various esters of linalool. Linalool has an important position in the ester-type perfumes and other cosmetic formulations. Linalool can generate citral through oxidation and can also be used for the synthesis of many other kinds of spices. linalool is a fragrant component of both lavender and coriander. It can be incorporated into cosmetics for perfuming, deodorant, or odor-masking activity. perfume use Linalool is one of the allergens of Ylang-Ylang oil (extract from Cananga odorata).
• Production method: 1. The commercial linalool is mainly isolated from natural essential oils including aloeswood oil, rosewood oil, coriander oil, and linalyl oil. Using efficient distillation column for fractionation can produce crude product of linalool with secondary fractionation obtaining finished product with a content being higher than 90%. Synthetic linalool can use β-pinene as raw material with pyrolysis yielding myrcene. Treatment with hydrogen chloride generates a mixture comprising linalyl chloride. Linalyl chloride can have reaction with potassium hydroxide (or potassium carbonate) to generate linalool. 2. It is existed in free form in camphor oil: using acetyl boric anhydride converting the linalool contained in camphor oil into acidic borate ester, and then through distillation, re-crystallization, and saponification to obtain the finished product. 3. Use 6-methyl-5-hept-ene-2-ketone to have condensation reaction with sodium acetylide to obtain dehydrolinalool, further undergoing reduction reaction at wet ether solution with metal sodium to obtain the linalool.
• Description: Linalool has a typical floral odor free from camphoraceous and terpenic notes.1 Synthetic linalool exhibits a cleaner and fresher note than the natural product. It can be prepared synthetically starting from myrcene or from dehydrolinalool.The optically active forms (d- and ι-) and the optically inactive form occur naturally in more than 2 0 0 oils from herbs, leaves, flowers, and wood; the ι-form is present in the largest amounts (80 - 85%) in the distillates from leaves of Cinnamomum cam phora var. orientalis and Cinnamomum camphora var. occidentalis and in the distillate from Cajenne rosewood; it also has been reported in: champaca, ylang-ylang, neroli, Mexican linaloe, ber gamot, lavandin, and others; a mixture of d- and ι-linalool has been reported in Brazil rosewood (85%); the d-form has been found in palmarosa, mace, sweet orange-flower distillate, petit grain, coriander (60 - 70%), marjoram, Orthodon linalooliferum (80%), and others; the inactive form has been reported in clary sage, jasmine, and Nectandra elaiophora.
• Physical properties: Properties. Racemic linalool is, similarly to the individual enantiomers, a colorless liquid with a floral, fresh odor, reminiscent of lily of the valley. However, the enantiomers differ slightly in odor. Together with its esters, linalool is one of the most frequently used fragrance substances and is produced in large quantities. In the presence of acids, linalool isomerizes readily to geraniol, nerol, and α-terpineol. It is oxidized to citral, for example, by chromic acid. Oxidation with peracetic acid yields linalool oxides, which occur in small amounts in essential oils and are also used in perfumery. Hydrogenation of linalool gives tetrahydrolinalool, a stable fragrance material. Its odor is not as strong as, but is fresher than, that of linalool. Linalool can be converted into linalyl acetate by reaction with ketene or with an excess of boiling acetic anhydride.

Technology Process of Linalool

There total 116 articles about Linalool 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%

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene (89155-68-0) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6)

Guidance literature:

With iodine; In methanol; microwave irradiation;

DOI:10.1081/scc-120026335

Reference yield: 99.8%

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6)

Guidance literature:

With hydrogen; PdAu in polystyrene-block-poly-4-vinylpyridine micelles; In toluene; at 90 ℃; for 0.316667h; under 760 Torr;

DOI:10.1006/jcat.2000.3039

Reference yield: 96.3%

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + vinylmagnesium chloride (3536-96-7) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Cooling with ice;

upstream raw materials:

2-methyl-3-buten-2-ol

geranyl chloride

ethanol

geranyl bromide

Downstream raw materials:

linalool acetate

(Z)-nerylacetone

trans geranyl acetone

3-(1-ethoxy)-3,7-dimethyl-1,6-octadiene

Refernces

• 1、 Gryaznov, V. M.,Maganyuk, A. P.,Karavanov, A. N.,Naumov, V. A.. "EFFECT OF PHASE COMPOSITION OF PALLADIUM-RUTHENIUM MEMBRANE CATALYST ON SELECTIVITY OF DEHYDROLINALOOL HYDROGENATION". . p. 853 - 855. Retrieved 1984.
• 2、 Bronstein, Lyudmila M.,Chernyshov, Dmitrii M.,Volkov, Ilya O.,Ezernitskaya, Marina G.,Valetsky, Peter M.,Matveeva, Valentina G.,Sulman, Esther M.. "Structure and Properties of Bimetallic Colloids Formed in Polystyrene-block-Poly-4-vinylpyridine Micelles: Catalytic Behavior in Selective Hydrogenation of Dehydrolinalool". . p. 302 - 314. Retrieved 2000.
• 3、 -. "Method for preparing allyl alcohol compound by reduction of propargyl alcohol compound". Paragraph 0059-0060. . Retrieved 2021/11/10.
• 4、 -. "Hydroxypyridine ligand and preparation method and catalytic application thereof (by machine translation)". Paragraph 0080-0082. . Retrieved 2020/05/11.