4-Hydroxy-3-methoxybenzyl alcohol
4-Hydroxy-3-methoxybenzyl alcohol
CAS: 498-00-0
Molecular Formula: C8H10O3
4-Hydroxy-3-methoxybenzyl alcohol - Names and Identifiers
| Name | 4-Hydroxy-3-methoxybenzyl alcohol |
| Synonyms | Vanillinol Vanillyl alcohol Vanillic alcohol α,4-Dihydroxy-3-Methoxytoluene 4-(hydroxymethyl)-2-methoxyphenol 4-Hydroxy-3-methoxybenzyl alcohol 3-Methoxy-4-hydroxybenzyl alcohol 4-Hydroxy-3-Methoxybenze-neMenthanol 3,4-Dihydroxybenzyl alcohol 3-Methyl ester 2-Hydroxy-5-(hydroxymethyl)anisole, 4-Hydroxy-3-methoxybenzyl alcohol, Vanillyl alcohol |
| CAS | 498-00-0 |
| EINECS | 207-852-4 |
| InChI | InChI=1/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3 |
4-Hydroxy-3-methoxybenzyl alcohol - Physico-chemical Properties
| Molecular Formula | C8H10O3 |
| Molar Mass | 154.16 |
| Density | 1.1690 (rough estimate) |
| Melting Point | 110-117 °C (lit.) |
| Boling Point | 237.52°C (rough estimate) |
| Flash Point | 143.2°C |
| JECFA Number | 886 |
| Water Solubility | Soluble in 95% ethanol (5 %), water, and oils. |
| Solubility | Soluble in hot water, ethanol, ether and benzene |
| Vapor Presure | 0.000216mmHg at 25°C |
| Appearance | White crystal |
| Color | Off-white to beige |
| BRN | 1910044 |
| pKa | 9.75±0.18(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents, strong acids. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.4620 (estimate) |
| MDL | MFCD00004659 |
| Physical and Chemical Properties | Soluble in hot water, ethanol, ether and benzene derived from North American spruce |
4-Hydroxy-3-methoxybenzyl alcohol - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29095090 |
| Hazard Note | Irritant |
4-Hydroxy-3-methoxybenzyl alcohol - Reference
| Reference Show more | 1. Liu, Mengyujie, et al. "Discovery and identification of proangiogenic chemical markers from Gastrodiae Rhizoma based on zebrafish model and metabolomics approach." Phytochemical Analysis 31.6 (2020): 835-845.https://doi.org/10.1002/pca.2949 2. [IF=3.21] Yuan Min et al."Rice straw enhancing catalysis of Pseudomonas fluorescens lipase for synthesis of citronellyl acetate."Bioprocess And Biosystems Engineering. 2021 Oct 22 3. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 4. [IF=2.772] Mengyujie Liu et al."Discovery and identification of proangiogenic chemical markers from Gastrodiae Rhizoma based on zebrafish model and metabolomics approach."Phytochem Analysis. 2020 Nov;31(6):835-845 5. [IF=6.475] Zhen Wu et al."How steaming and drying processes affect the active compounds and antioxidant types of Gastrodia elata Bl. f. glauca S. chow."FOOD RESEARCH INTERNATIONAL. 2022 Jul;157:111277 |
4-Hydroxy-3-methoxybenzyl alcohol - Reference Information
| FEMA | 3737 | VANILLYL ALCOHOL |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| vanilla alcohol | functional classification: the molecular formula of food flavor vanilla alcohol is C8H10O3, the United Nations Food and Agriculture Organization/World Health Organization Joint Expert Committee on Food Additives, the European Commission, the American Association of Flavor and Extract Manufacturers, etc. approved it to be used as a food flavor in various foods according to production needs. Dosage and scope of use: prepared food flavors are used in various foods (except for food categories in Table B .1 of GB 2760-2014), and the dosage is appropriate according to production requirements. Process necessity: vanillin is a food additive made from vanillin through chemical reaction. The substance can improve the taste of food, and its quality specifications are implemented in accordance with the relevant contents of the announcement. |
| Application | 4-hydroxy-3-methoxybenzyl alcohol, also known as vanillin, is a colorless or white crystalline solid, slightly soluble in water, Soluble in oil. It has sweet aroma, cream, phenol aroma, vanilla and coconut aroma. It can be used as organic synthesis intermediate and pharmaceutical intermediate, and is mainly used in laboratory research and development process and chemical medicine research and development process. |
| preparation | 1) take 10kg of fresh and undamaged fruiting body of chrysalis mushroom, slice it and soak it with 30L 95% ethanol for 7 days (the ratio of fruiting body to ethanol is 1:3, so that ethanol is completely soaked in fruiting body of chrysalis mushroom), filter it to obtain filtrate, and recover solvent under reduced pressure, 30L 95% ethanol was added to the filter residue for ultrasonic extraction for 3 times, each extraction for 2 hours. Concentrate under reduced pressure to obtain 95% ethanol extract. The 65% ethanol extract was obtained by using the same method and concentrated under reduced pressure to obtain 65% ethanol extract. After alcohol extraction, 30L of distilled water was added and 1800HZ ultrasonic extraction was carried out for three times, each time for 2 hours. Water extract 538g was obtained by decompression concentration. Among them, the above decompression recovery conditions are 0.25MPA, temperature 30 ℃; The above ultrasonic extraction conditions are 800HZ, ultrasonic 45min, temperature 30 ℃. The two parts of alcohol extract are combined to obtain 84.5g, the combined extract 84.5g is kneaded and dispersed in 500ml of pure water, petroleum ether (the ratio of water to petroleum ether is 1:1) is added to a 2000ml separatory funnel, the extract dispersion is added to the separatory funnel, extracted for 5 times, and the extract is combined and concentrated to obtain 10.0g of petroleum ether site. Then add ethyl acetate to the separatory funnel (the ratio of water to ethyl acetate is 1:1), extract 6 times, and concentrate the extract to obtain 6.0g of ethyl acetate. Add n-butanol (the ratio of water to n-butanol is 1:1) to the separatory funnel, extract 5 times, and concentrate the extract to obtain 60.0g of n-butanol. Among them, the above extraction conditions are: extraction pressure is 40MPa, extraction temperature is 35 ℃, extraction time is 2h. 2) 10.0g of the obtained petroleum ether site was separated by medium-pressure silica gel column rapid chromatography, the petroleum ether-ethyl acetate system (100:0~0:100) was eluted by gradient, the eluent was detected by thin layer chromatography, similar fractions were combined, and the solvent was recovered to obtain a total of 9 components of A ~ I. Component D was separated by medium pressure silica gel chromatography to obtain D1 and D2. D1 recrystallizes to obtain 20mg of needle-like compound 3. D2 was separated by multiple times of medium pressure silica gel chromatography and Sephadex LH-20 column chromatography to obtain 10mg of white solid compound 2. Component E was separated by multiple medium-pressure silica gel chromatography and Sephadex LH-20 column chromatography to obtain 5mg of yellow-green oily solid compound 1. Among them, the rapid chromatographic separation conditions of medium-pressure silica gel column in the above petroleum ether site are as follows: 120-130 μm chromatography silica gel is used as silica gel column, the diameter-to-height ratio of silica gel is 1:8, and the flow rate is 40ml/min. Among them, the Sephadex LH-20 column chromatographic separation conditions are as follows: acidified methanol is used as eluent, the concentration is 25%(Ph is adjusted at 4), and the flow rate is 0.5 ml/min. The physicochemical properties of the separated and purified compound components are identified by conventional physical detection methods: the detection methods are: EIS-MS, H-NMR and C- NMR. The detection method is the same as that of Pharmacopoeia 2015 edition. One of the compounds was vanillin/4-hydroxy-3-methoxybenzyl alcohol (4-hydroxy-3-methoxy-benzyl alcohol), white solid. Easily soluble in acetone, chloroform and methanol, insoluble in water. |
| toxicity | GRAS(FEMA). |
| usage limit | FEMA: baked goods, cold drinks, soft candy, gel, pudding and alcohol-free drinks, all 12.0 mg/kg. |
Last Update：2024-04-09 21:04:16
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View History
4-Hydroxy-3-methoxybenzyl alcohol
326902-03-8
5-醛基噻吩-2-甲酸甲酯
108712-07-8
Benz[a]acephenanthrylene-6,7-dione
[3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL](4-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]PIPERAZINO)METHANONE
4,6-Dioxa-2-azabicyclo[3.2.0]heptan-3-one, 2-acetyl-7,7-dimethyl-
2-甲基-2-丙烯酸钠盐
Scopolin
2-Propenoic acid, 3-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, (2Z)-
326902-03-8
5-醛基噻吩-2-甲酸甲酯
108712-07-8
Benz[a]acephenanthrylene-6,7-dione
[3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL](4-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]PIPERAZINO)METHANONE
4,6-Dioxa-2-azabicyclo[3.2.0]heptan-3-one, 2-acetyl-7,7-dimethyl-
2-甲基-2-丙烯酸钠盐
Scopolin
2-Propenoic acid, 3-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, (2Z)-