CAS number：106-22-9
molecular formula：C10H20O
molecular weight：156.27
EINECS number：203-375-0

English synonyms

2,6-DIMETHYL-2-OCTEN-8-OL;(+/-)-CITRONELLOL;CITRONELLOL;CITRONELLOL PRIME;CITRONELLOL EXTRA;CITRONELLOL 80;CITRONELLOL 90/92;CITRONELLOL 96

Related categories

Alcohols, aldehydes, ketones; biochemical reagents-carbohydrates; organic chemical raw materials; flavors and fragrances; agricultural and environmental standards; flavors and fragrances; traditional Chinese medicine reference substances; natural plant essential oils; food additives; edible flavors (flavoring agents); natural Equivalent fragrances and artificial fragrances; synthetic fragrances; daily necessities; fragrances and fragrances; other oxygenated compounds; fragrances for cosmetics; analytical standards; plant extracts; general reagents; alcohols; fragrances and fragrances; pharmaceutical raw materials; reference substances; natural forest essential oils ;AcyclicMonoterpenes;Biochemistry;Terpenes;AlphabeticalLiChemicalbookstings;C-D;FlavorsandFragrances;Acyclic;Alcohols;Alkenes;BuildingBlocks;C9toC10;ChemicalSynthesis;OrganicBuildingBlocks;OxygenCompounds;
Raw materials; chemical raw materials; cosmetic additives, fragrances, flavors; chemical materials; pharmaceuticals, pesticides and dye intermediates; monomer fragrances; general biochemical reagents - natural products; fragrances; aldehydes, alcohols, ketones; organic intermediates; bc0001

Introduction

Citronellol, also known as vanillyl alcohol, also known as β-androcallisol, is mainly derived from essential oils such as rose, lemongrass, geranium, eucalyptus, and lemon balm. It also contains a small amount of fragrance in high-grade ginger essential oil. malol. Citronellol is an acyclic monoterpenoid, the simplest type of monoterpene alcohols, which can be used to formulate a variety of fragrances and perfumes, with a more elegant rose aroma than geraniol. In addition, citronellol has also been clinically proven to have various pharmacological activities, which can be used for anti-inflammatory, anticonvulsant, analgesic, and cholesterol lowering. Citronellol is also an important intermediate in the total synthesis of various chiral compounds.

Chemical properties

Colorless oily liquid with a special aroma like fresh rose and bitter taste. There are three natural products of d-, dl- and l-, l-citronellol is rhodiol (rhodinol; see this article), commonly known as citronellol, refers to citronellol. The boiling point of 225 ° C, the flash point of 102 ° C. Soluble in ethanol and most non-volatile oils and propylene glycol, insoluble in glycerol, insoluble in water. Natural citronellol (d-type) exists in more than 70 essential oils such as citronella oil and geranium oil.

 Use

●  GB2760-96 stipulates that it is allowed to use edible spices. For the preparation of a variety of flavors, a wide range of uses.

●  Used to extract geraniol or citronellal, also used as insecticide, mosquito repellent and soap essence

●  Widely used in the preparation of perfume essence, soap and cosmetic essence, etc.

●  It is the base aroma of rose-type essence, and is also commonly used to sweeten the fragrance of flowers, such as lily of the valley, lilac, sweet-scented osmanthus and other fragrances. It is used to prepare a variety of heavy and floral fragrances. It is often used in combination with geraniol, geraniol and phenylethyl alcohol to form a rose base. It can also be used in Chemicalbook edible flavors such as roses, strawberries, raspberries and other berries, citrus fruits, and peaches.

●  Extracted from geraniol, it is a common flavor and spice used in winemaking; it is also used to repel insects.

●  Citronellol is the most commonly used fragrance and is most suitable for rose fragrance. It can also be used as a citrus fragrance and a raw material for many citronellol esters. malaldehyde. Citronellol is an indispensable raw material for the preparation of various rose-based floral essences, and can be used in almost all cosmetics. As an edible spice, according to the provisions of Japan's "Food Additives Official Book", the purity is required to be more than 94%, and it should not be used for purposes other than flavoring.

Production method

●  (1) D- and racemic citronellol are manufactured from the citronellal moiety in essential oils. D-citronellal obtained by distillation from Java vanilla oil is converted into D-citronellol by contact hydrogenation with Raney nickel catalyst. Likewise, racemic citronellol is obtained from the racemic citronellal moiety in lemon eucalyptus oil.
(2) Manufactured from dextro- or racemic geraniol in essential oils. Geranium sinensis obtained from Java citronella oil is obtained by catalytic hydrogenation, followed by fractional distillation. Select Raney cobalt as a catalyst to hydrogenate the 2-position double bond.
(3) It is obtained by partial hydrogenation of the mixture of synthetic geraniol and nerol; or it is produced by reacting isopropanol with copper siglate activated by barium under pressure at 180°C. The yield of this method was 90%.
(4) L-citronellol is produced from optically active pinene. Hydrogenation of α- or β-pinene to (-)-cis-pinene, thermal cracking Chemicalbook into (+)-3,7-dimethyl-1,6-octadiene, with triisobutylaluminum or Diisobutylaluminum hydride is used, and then the resulting aluminum alkoxide is oxidized and hydrolyzed to obtain citronellol with a purity of 97%.

●  It is derived from the reduction of citronellal. In anhydrous ethanol, add metal aluminum scraps and aluminum amalgam, heat, and when the aluminum dissolves, slowly add the mixture of citronellal and anhydrous butanol under stirring, heat at 50-80 ° C for 3-6 hours, and cool , dilute with water to separate the alcohol layer, and then use vacuum distillation to distill off butanol to obtain citronellol. It is obtained by reducing geraniol with sodium metal in diethyl ether, benzene or other organic solvents under the condition that hydrogen is continuously introduced. Add catalyst ferrous sulfate to the ethanol solution, hydrogenate citral under the catalysis of platinum black to obtain geraniol, and then obtain citronellol by the above method.

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