7-Hydroxycitronellal
7-Hydroxycitronellal
CAS: 107-75-5
Molecular Formula: C10H20O2
7-Hydroxycitronellal - Names and Identifiers
| Name | 7-Hydroxycitronellal |
| Synonyms | LAURINE FEMA 2583 7-Hydroxycitronellal HYDROXYCITRONELLAL(AS) 3,7-Dimethyl-7-Hydroxyoctanal 7-hydroxy-3,7-dimethyl-octana 3,7-dimethyl-7-hydroxy-1-octana OCTANAL, 7-HYDROXY-3,7-DIMETHYL 7-Hydroxy-3,7-dimethyloctan-1-al 1-Octanal, 3,7-dimethyl-7-hydroxy- |
| CAS | 107-75-5 |
| EINECS | 203-518-7 |
| InChI | InChI=1/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3/t9-/m0/s1 |
| InChIKey | WPFVBOQKRVRMJB-UHFFFAOYSA-N |
7-Hydroxycitronellal - Physico-chemical Properties
| Molecular Formula | C10H20O2 |
| Molar Mass | 172.26 |
| Density | 0.923g/mLat 25°C(lit.) |
| Melting Point | 22-23 °C |
| Boling Point | 257°C(lit.) |
| Flash Point | >230°F |
| JECFA Number | 611 |
| Water Solubility | 35g/L at 20℃ |
| Solubility | Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly) |
| Vapor Presure | 0.547Pa at 20℃ |
| Appearance | Colorless liquid |
| Specific Gravity | 0.93 |
| Color | Clear colorless |
| pKa | 15.31±0.29(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Stability | Air Sensitive |
| Refractive Index | n20/D 1.448(lit.) |
| MDL | MFCD00014681 |
| Physical and Chemical Properties | Colorless to light yellow transparent liquid. With the aroma of Lily and Lily. Solubility 75%. 6 to 7 times soluble in ethanol. |
7-Hydroxycitronellal - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R38 - Irritating to the skin R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 1 |
| RTECS | RG7850000 |
| HS Code | 29124990 |
7-Hydroxycitronellal - Nature
Open Data Verified Data
colorless viscous liquid with strong Lily aroma. Soluble in ethanol, propylene glycol and most non-volatile oils, insoluble in water, mineral oil and glycerin. It is easily oxidized in air and unstable in alkaline medium.
Last Update：2024-01-02 23:10:35
7-Hydroxycitronellal - Preparation Method
Open Data Verified Data
from citronellal and water addition, refined.
Last Update：2022-01-01 10:07:45
7-Hydroxycitronellal - Use
Open Data Verified Data
widely used in Lily of the valley, orchid, Jasmine, clove and other essences, in perfume, powder and other cosmetic essences dosage as high as 20%. In the chewing gum dosage of 16mg/kg; 13mg/kg in cold drinks; Baked food 10 mg/kg; Candy 9.4mg/kg; Soft drinks in 3. 5 mg/kg; 0.3 mg/kg in Class D.
Last Update：2022-01-01 10:07:45
7-Hydroxycitronellal - Reference Information
| FEMA | 2583 | HYDROXYCITRONELLAL |
| LogP | 1.68 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | hydroxycitronellal, English name is HYDROXYCITRONELLAL, alias: hydroxyvanillin, 7-hydroxyvanillin, 7-hydroxy-3, 7-dimethyl-1-octanal. Hydroxycitronellal in cosmetics, skin care products in the main role is flavors and fragrances, risk coefficient is 7, pay more attention to the reaction, for pregnant women generally have no effect, hydroxycitronellal does not cause acne. Widely used in lily-of-the-valley, lily, hosta, jasmine and narcissus and other floral flavors, it has the effect of improving the sensory quality of cosmetics, but at the same time it has certain toxicity. |
| Main properties | Instable to acids and bases. It is easy to oxidize in the air. Easy to polymerize, antioxidant 2, 6-di-tert-butyl-4-methylphenol can be added during storage. This product contains aldehyde-based tertiary alcohol groups, so it has the characteristics of both. When hydroxycitronellal reproduces with sodium bisulfite, it can form a compound of sodium bisulfite. |
| use | hydroxycitronellal has a similar bodhi when diluted; lily of the valley and fresh grass aroma, widely used in lily of the valley; orchid; jasmine; lilac and other flavors, in perfume; Fragrance powder and other cosmetic flavors, the dosage is as high as 20%, which is one of the most valuable spices. This product is a edible spice allowed by GB2760-86 regulations in our country, and is mainly used to prepare citrus. Watermelon; Cherry and other melon and fruit essence. Because the product is easy to oxidize, antioxidant 3, 6-di-tert-butyl-4-methylphenol can be added for stabilization. Hydroxycitronellal is unstable in alkalinity, so its acetals are used in soap flavors, such as dimethylal, etc. Sometimes hydroxycitronellal and benzyl alcohol are stored and used in the form of hemiacetal. used to prepare narcissus, lily of the valley, jasmine and hyacinth fragrance is a multi-purpose fragrance, which can be used for various floral types and many non-flower types. Used for lily of the valley, bodhi, lily and the same aroma of rabbit ear grass flower, lilac and other types, can make the aroma delicate. It can be used in perfume essence to give flower fragrance. You can also use soap flavors and flavors such as orange blossom and white lemon. Pure quality can be used in an appropriate amount of edible essence, which can give flower fragrance, thicken and thicken, and make the fragrance round. Hydroxycitronellal is a food spice allowed to be used in my country's "Hygienic Standards for the Use of Food Additives". It is mainly used to prepare cherry, citrus, watermelon and other melon and fruit flavors. The amount used in chewing gum is 16 mg/kg. 13 mg/kg in cold drinks; Baked food is abnormal 10 mg/kg; 9.4 mg/kg in candy; 3.5 mg/kg in soft drinks; 0.3 mg/kg in pudding. the product has fragrance similar to bodhi, lily of the valley and fresh grass when diluted. it is widely used in lily of the valley, orchid, jasmine, lilac and other flavors. it is one of the most valuable spices in cosmetics such as perfume and powder, which is as high as 20%. This product is an edible spice allowed by GB2760-86 regulations in our country. It is mainly used to prepare citrus, watermelon, cherry and other melon and fruit flavors. Because the product is easy to oxidize, antioxidant 3, 6-di-tert-butyl-4-methylphenol can be added for stabilization. Hydroxycitronellal is unstable in alkalinity, so its acetals are used in soap flavors, such as dimethylal, etc. Sometimes hydroxycitronellal is stored and used in the form of hemiacetal with benzyl alcohol, phenylethyl alcohol and citronellol. Hydroxycitronellal is also used to prepare other fragrances, such as 1-amino-7-hydroxy-3, 7-dimethyloctane and methyl o-hydroxycitronella parabenoate. Rats have been fed with feed containing 0.5% for two years, and no abnormal phenomenon has been found. GB 2760-96 specifies edible spices that are allowed to be used. It is mainly used to prepare citrus, watermelon, cherry and other melon and fruit flavors, and also used as fixative and flavoring aids. |
| Preparation method | It is prepared by adding water to the double bond with citronellal. The hydration reaction of citronellal is carried out in the presence of inorganic acid, but citronellal is unstable in acidic medium. Sodium bisulfite, amines, lower fatty anhydrides, etc. are required to protect the aldehyde group. After the hydration reaction is over, The aldehyde group is restored under the action of the reaction reagent. It is the most common method to protect the aldehyde group of citronellal and sodium bisulfite to form bisulfite compound, and then hydrate it. Then use dried sodium carbonate to decompose the bisulfite compound in toluene to precipitate hydroxycitronellal. Citronellal is obtained by catalytic hydrogenation of citral or essential oils and products containing citral. Citronellal is hydrated with sodium bisulfite solution. Then sodium carbonate is added to neutralize the remaining hydrochloric acid, and when the acid content in the material is 0.5-1%, the organic impurities are extracted with toluene. After the toluene extract is separated, toluene is added to the hydration product, and dried sodium carbonate is added to decompose the bisulfite compound of hydroxycitronellal. At this time, the precipitated aldehyde is extracted by toluene, and the toluene solution is taken to recover toluene. The residue is purified by vacuum distillation to obtain the product hydroxycitronellal. |
| Production method | The adduct of citronellal and bisulfite is dissolved in concentrated sulfuric acid at -20 ℃ to form citronellal sulfate, and then decomposed in sodium carbonate solution. At a lower temperature, citronellal reacts with acetic anhydride and sodium acetate to form citronellal acetate, and then hydrolyze and treat with dilute lye to obtain crude product, which is purified with acid sulfite. The citronellal isolated from Java-type citronella oil or lemon eucalyptus leaf oil in China is obtained by hydration substitution and refined steaming (or distillation). citronellal is reacted with sodium bisulfite under cooling, then hydrated with 14% ~ 15% hydrochloric acid solution at 35 ℃, and sodium carbonate is added to neutralize the remaining hydrochloric acid until the acid content in the material is 0.5% ~ 1%. First use a small amount of toluene extraction to remove organic impurities, and then add toluene and dried sodium carbonate to the hydrate to decompose bisulfite, and the generated hydroxycitronellal is extracted by toluene. The toluene extract first recovers toluene, and then distilled under reduced pressure to obtain the product hydroxycitronellal. |
Last Update：2024-04-09 21:11:58
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