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Linalool CAS NO.78-70-6
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- Linalool
- Linalool
- 78-70-6
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| Linalool Chemical Properties |
| bp | 199 °C |
| density | 0.87 g/mL at 25 °C(lit.) |
| vapor pressure | 0.17 mm Hg ( 25 °C) |
| FEMA | 2635 |
| refractive index | n20/D 1.462(lit.) |
| Fp | 174 °F |
| storage temp. | 2-8°C |
| Water Solubility | 1.45 g/L (25 ºC) |
| Merck | 14,5495 |
| BRN | 1721488 |
| Stability: | Stable. Incompatible with strong oxidizing agents. Combustible. |
| CAS DataBase Reference | 78-70-6(CAS DataBase Reference) |
| NIST Chemistry Reference | 2,6-Dimethylocta-2,7-dien-6-ol(78-70-6) |
| EPA Substance Registry System | 1,6-Octadien-3-ol, 3,7-dimethyl-(78-70-6) |
| Safety Information |
| Hazard Codes | Xi,Xn |
| Risk Statements | 36/37/38-20/21/22 |
| Safety Statements | 26-36 |
| WGK Germany | 1 |
| RTECS | RG5775000 |
| HS Code | 29052210 |
| Hazardous Substances Data | 78-70-6(Hazardous Substances Data) |
| Linalool Usage And Synthesis |
| Spices | Linalool is a kind of terpene alcohols and is one kind of famous perfume compounds. It is the mixture of two isomers (α-linalool and β- linalool). It is extracted from camphor oil (from camphor tree) or synthesized from the α-pinene or β-pinene contained in turpentine. It is colorless oily liquid with sweet and tender fresh flowers and a fragrance of Convallaria majalis. It is easily soluble in organic solvents such as ethanol, ethylene glycol and diethyl ether but insoluble in water and glycerol. It is easily subject to isomerization and is relatively stable in alkali. It has a density (25 ℃) of 0.860 ~ 0.867, the refractive index (20 ℃) of 1.4610 ~ 1.4640, optical rotation (20 ℃) of -12 ° ~ -18 °, the boiling point being 197 ~ 199 ℃, and the flash point (open ended) of 78 ℃. Linalool with alcohol content higher than 95% is an important spices for floral fragrance used for perfumes, soaps and other fragrance industry. It is also widely used in flowers oils of lending lily, lilac, sweet pea, and orange blossom as well as the compound perfume of amber incense, oriental fragrance, and aldehyde-type fragrance, cosmetics perfumes and food flavor. It can also be used as the spices of lemon, lime, orange, grape, apricot, pineapple, plum, peach, cardamom, cocoa, and chocolate. Drug containing 92.5% alcohol content is used as the raw material drugs in the pharmaceutical industry for producing isophytol which is an important intermediate in the preparation of vitamin E. It can also be used as raw material for producing valuable spices linalyl acetate and some other esters. Linalool belongs to open chain terpene tertiary alcohol. It has two double bonds. However, it contains an asymmetric carbon atom, so it has three kinds of optical isomers. In Nature, all three kinds of isomers are present with the amount of I-body being the highest, accounting for 70% to 80% of the total amount of the three. I- body is mostly presented in linalool oil (containing about 80 to 90%), champa, lavender oil, lime oil, neroli oil, clary sage oil, aloeswood oil, lemon oil, rose oil, cananga orodrata oil and some other kinds of essential oil; its d-body is mostly presented in coriander oil (containing about 60% to 70%), sweet orange oil, nutmeg oil, palmarosa oil and other kinds of essential oil; its dl-form is mainly presented in the essential oils of clary sage and jasmine. All the three kinds are transparent colorless oily liquid with lilies and citrus-like fragrance. In addition, because of the close distance between its hydroxy group and allyl group, its chemical nature is very influential. In the presence of sodium metal in ethanol solution, it can be easily be reduced to generate dihydro-myrcene; in the presence of a platinum catalyst or Raney nickel catalyst, it can be reduced to the tetrahydro linalool to become saturated alcohol. Owing that it is a kind of tertiary alcohol, in strongly acidic medium, it can subject to isomerization; in dilute acid medium, it undergoes dehydration to become esters. It is stable in alkaline medium. The LD50 of oral administration for Rat is 2790 mg /kg. |
| Content Analysis |
Take 10 mL of sodium sulfate pre-dried sample and put it into a 125 mL of glass-stoppered Erlenmeyer flask pre-cooled by an ice bath. Add 20 mL of dimethylaniline (toluidine product) in cold oil and mix thoroughly. Add 8 mL of acetyl chloride and 5 mL of acetic anhydride, cool for several minutes, then place at room temperature for 30min, then immerse the flask in a water bath and maintained for 16h at 40 °C ± 1 °C; Apply ice-water for washing acetyl oil for three times with 75 mL each time. Then repeatedly wash with 25 mL of 5% sulfuric acid solution until the separated acid layer no longer exhibiting cloudy-like or doesn’t have further dimethylaniline odor coming out so that dimethylaniline was further removed. First apply 10 mL of 10% sodium carbonate solution for washing acetylated oil, followed by successive washing with water until washing to being neutral to litmus. After complete drying with anhydrous sodium sulfate, accurately weigh the acetylation oil of about 1.2g, and then measure it according to the "ester assay" (OT-18). Linalool (C10H18O) content (L) is calculated as follows; L = 7.707 (b-s) /W=0.021 (b-s) Where L-- linalool content, %; b- the consumed volume of 0.5 mol/L of hydrochloric acid in blank test, Mi; s-- the consumed volume of 0.5 mol/L of hydrochloric acid for titration of the sample solution, ml; IV-sample sample, g. Method II, measure the amount using non-polar column protocol based on the Gas Chromatography Method (GT-10-4). The above information is edited by the chemicalbook of Dai Xiongfeng. |
| Toxicity |
Adl 0 ~ 0.5 mg / kg (FAO / WHO.1994). GRAS (FDA, §182.60, 2000). LD50 2790 (rat, oral administration). |
| Limited use | FEMA (mg/kg): Soft drinks 2.0; cold drink 3.6; candy 8.4; Bakery 9.6; pudding Class 2.3; gum 0.80 to 90; meat 40. |
| The maximum allowed amount as food additives or maximum allowable residue amount |
|
| Chemical Properties | It is colorless liquid with fragrance similar with bergamot. It is insoluble in water, but miscible with ethanol and ether. |
| Application |
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. |
| 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. |
| Chemical Properties | liquid |
| Usage | perfume use |
