Name | Geranic acid |
Synonyms | Geranic acid 3,7-dimethylocta-2,6-dienoate geranic acid, mixture of isomers 3,7-dimethylocta-2,6-dienoic acid (2E)-3,7-dimethylocta-2,6-dienoic acid (2Z)-3,7-dimethylocta-2,6-dienoic acid |
CAS | 459-80-3 |
EINECS | 207-299-9 |
InChI | InChI=1/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/p-1 |
Molecular Formula | C10H16O2 |
Molar Mass | 168.24 |
Density | 0.97 g/mL at 25 °C(lit.) |
Melting Point | 185-186 °C (decomp) |
Boling Point | 295.3°C at 760 mmHg |
Flash Point | 201.1°C |
Vapor Presure | 0.000373mmHg at 25°C |
Appearance | Colorless to yellow liquid |
pKa | 5.17±0.33(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
MDL | MFCD00036493 |
Physical and Chemical Properties | EPA Chemical Information 2,6-Octadienoic acid, 3,7-dimethyl- (459-80-3) |
Use | Possible uses: orange, tea, mint, ripe fruit and melon flavor. |
Risk Codes | R21 - Harmful in contact with skin R38 - Irritating to the skin |
Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
WGK Germany | 3 |
RTECS | RG5380000 |
FLUKA BRAND F CODES | 10 |
TSCA | Yes |
FEMA | 4121 | GERANIC ACID |
solubility | H2O: insoluble |
JECFA Number | 1825 |
BRN | 1763804 |
overview
P> folic acid, also known as rosial bovine acid, is a mixture of α-and β-isomers, with a relative density of 0.9518 (19.4/4 ℃), a boiling point of 158 ℃(14 × 133.322Pa), and a refractive index of 1.4870(20.2 ℃). Oily liquid, insoluble in water, soluble in alcohol and ether. Beta-vanifolate is present in Chinese rose oil. It is used in the spice industry. It can be made from citral through mild oxidation.application
P> folic acid, also known as bull acid, is a plant extract with fresh oil and green fragrance and apple-like aroma of fruits and vegetables. it can not only be widely used in daily chemical flavors such as soap and detergent, but also is a very important daily chemical flavor when preparing high-grade perfume.action
Seafic acid can effectively reduce the content of acrylamide in fried foods: Seafic acid acts on the key steps of the asparagine pathway produced by acrylamide, which can not only block the production of acrylamide, but also promote the already produced The digestion of acrylamide effectively reduces the content of acrylamide, thereby maintaining a higher content of amino acids, flavonoids and saponins, and improving the quality of fried foods.
Preparation
Oxidation of citral to prepare folic acid:
there are three different reports on the preparation of vanic acid by oxidizing citral with sodium chlorite, which mainly includes 2-methyl -2-butene and tert-butanol as solvent, 2-methyl -2-butene and acetone as solvent, and DMSO as solvent. among them, the yield of DMSO as solvent is relatively low, only 46%, so we mainly examine the first two methods.
(1) Use 2-methyl -2-butene and tert-butanol as solvents. 5.2g of citral is dissolved in a mixed solvent of 55 mL2-methyl -2-butene and 150mL of tert-butanol, cooled to 10 ℃.27.8g of 80% sodium chlorite is dissolved in 100mL of water, 44.7gNaH2PO4 is dissolved in 150mL of water, and added dropwise to citral solution. Control the droplet acceleration so that the reaction temperature does not exceed 35 ℃ and the two are almost finished at the same time. After dripping, stir at room temperature, TLC tracks until the raw material point disappears. Add 100mL of ethyl acetate to dilute and stratify, and the aqueous phase is extracted twice with 200mL of ethyl acetate; After the organic phase is dried, filtered with anhydrous sodium sulfate, and the solvent is distilled under reduced pressure, the crude product is obtained by passing through the column with ethyl acetate and petroleum ether to obtain 4.2g of cilifolate product with a yield of 73.5%.
(2) Use 2-methyl -2-butene and acetone as solvents. 5.2g of citral is dissolved in a mixed solvent of 55 mL2-methyl -2-butene and 210mL of acetone, cooled to 10 ℃.27.8g of 80% sodium chlorite is dissolved in 100mL of water, 44.7gNaH2PO4 is dissolved in 150mL of water, and added dropwise to citral solution at room temperature. Control the droplet acceleration so that the reaction temperature does not exceed 35 ℃, and the two are almost dripped at the same time. After dripping, stir at room temperature, TLC tracks until the raw material point disappears. Add 100mL ethyl acetate to dilute and stratify, the aqueous phase is extracted twice with 200mL ethyl acetate, the organic phase is dried with anhydrous sodium sulfate, and filtered. After the solvent was distilled under reduced pressure, the crude product was passed through the column with ethyl acetate and petroleum ether to obtain 4.8g of cilifolate product with 83.9% yield.