122-48-5
zingerone
CAS: 122-48-5
Molecular Formula: C11H14O3
122-48-5 - Names and Identifiers
| Name | zingerone |
| Synonyms | zingerone Gingerone [0]-Paradol (0)-paradol 4-(4-hydroxy-3 Vanillylacetone 3-Methoxy-4-hydroxybenzylacetone 3-methoxy-4-hydroxy-benzylacetone 4-(4-hydroxy-3-methoxyphenyl)-2-butanon 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one 4-(3-methoxy-4-hydroxyphenyl)-2-butanone |
| CAS | 122-48-5 |
| EINECS | 204-548-3 |
| InChI | InChI=1/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3 |
| InChIKey | OJYLAHXKWMRDGS-UHFFFAOYSA-N |
122-48-5 - Physico-chemical Properties
| Molecular Formula | C11H14O3 |
| Molar Mass | 194.23 |
| Density | 1.14g/mLat 25°C(lit.) |
| Melting Point | 40-41°C(lit.) |
| Boling Point | 141°C0.5mm Hg(lit.) |
| Flash Point | >230°F |
| JECFA Number | 730 |
| Solubility | Soluble in ether and dilute alkali, slightly soluble in water and petroleum ether. |
| Vapor Presure | 0.000143mmHg at 25°C |
| Appearance | Crystals (from acetone, petroleum ether, ether-petroleum ether) |
| Color | White to Pale Yellow Low-Melting |
| Merck | 14,10166 |
| pKa | 10.03±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | n20/D 1.541(lit.) |
| MDL | MFCD00048232 |
| In vitro study | Vanillylacetone is similar in chemical structure to other fragrance chemicals such as vanillin and eugenol. It is used as a flavoring additive in sesame oils and fragrances to introduce a spice flavor. Ginger does not contain vanillylacetone; Ginger is converted to gingerol by cooking, which is the current example of conversion to vanillylacetone by an aldol condensation reaction. Vanillylacetone may be the active ingredient of ginger to exert antidiarrheal effect. |
122-48-5 - Risk and Safety
| 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 | 2 |
| RTECS | EL8900000 |
| TSCA | Yes |
| HS Code | 29333999 |
122-48-5 - Reference
| Reference Show more | 1. Xiao-Fei Shang, Li-Xia Dai, Ying-Qian Liu, Zhong-Min Zhao, Jun-Cai Li, Guan-Zhou Yang, Cheng-Jie Yang,Acaricidal activity and enzyme inhibitory activity of active compounds of essential oils against Psoroptes cuniculi,Veterinary Parasitology,Volume 267, 2. [IF=2.738] Xiao-Fei Shang et al."Acaricidal activity and enzyme inhibitory activity of active compounds of essential oils against Psoroptes cuniculi."Vet Parasitol. 2019 Mar;267:54 3. [IF=9.381] Xinyu Meng et al."A family of chitosan-peptide conjugates provides broad HLB values, enhancing emulsion’s stability, antioxidant and drug release capacity."Carbohyd Polym. 2021 Apr;258:117653 4. [IF=5.813] Yali Li et al."Synergistic effect of hypocrellin B and curcumin on photodynamic inactivation of Staphylococcus aureus."Microb Biotechnol. 2021 Mar;14(2):692-707 5. [IF=5.81] Cui Lihua et al."Chaihu Guizhi Ganjiang Decoction Ameliorates Pancreatic Fibrosis via JNK/mTOR Signaling Pathway."Front Pharmacol. 2021 Jun;0:1369 |
122-48-5 - Reference Information
| FEMA | 3124 | ZINGERONE |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| food flavor | ginger ketone, also known as ginger ketone and vanillyl acetone, is a kind of food flavor that can be prepared in an appropriate amount according to the production requirements according to the provisions of China's "Hygienic Standard for the Use of Food Additives" (GB 2760-1996). Its chemical name is 4-(4-hydroxy-3-methoxyphenyl)-2-butanone. Light yellow or light amber crystals (acetone, petroleum ether or ether-petroleum ether), left at room temperature for a long time to form a viscous liquid. There is a strong ginger-like spicy smell and ginger-like spicy taste, with sweet, spicy, rich and heavy flower fragrance, lasting fragrance. Relative density 1.138~1.139(25 ℃), melting point 40~41 ℃, boiling point 290 ℃(102 ℃), refractive index 1.544~1.545. It can be dissolved in 50% ethanol in a ratio of 1:1, slightly soluble in water and petroleum ether, and soluble in dilute alkali. Slowly volatilized in the steam. When heated, the silver nitrate ammonia solution can be reduced; the alcohol solution with ferric chloride becomes green. Separated from the essential oil of ginger (Zingiber officinale), ginger ketone is the main component of ginger oil. It is prepared by hydrogenation of vanillin and acetone after condensation reaction. Used as a sweetener and edible flavor for rich flavor. It can produce "leather" and "tobacco" flavor in fragrant products. It is not easy to change color. Gingerone can be used in the formula of daily chemical essence, mainly as a sweetener for rich flavor, with a small amount and a small application range. IFRA has no restrictions. ginger ketone is recognized as GRAS by FEMA, FEMA number 3124, and is approved by FDA for consumption. it is listed by the European Council in the list of artificial spices that can be used in food and are harmless to human health at the dosage level of 15 mg/kg. Gingerone can be used in edible flavors and flavored product formulations. FEMA stipulates that the maximum reference dosage of ginger ketone is soft drink, 6.9 mg/kg; Ice cream, ice food, 7.8 mg/kg; Candy, 11 mg/kg; Baked food, 11 mg/kg; Chewing gum, 15 mg/kg. |
| content analysis | determined by non-polar column method of gas chromatography (GT-10-4). |
| toxicity | GRAS(FEMA). LD502.58g/kg (rat, oral). |
| usage limit | FEMA(mg/kg): soft drink 6.9; Cold drink 7.8; Candy, baked goods, 11.0; Gum sugar 15.0:FDA, 172.515: right amount is limited. |
| biological activity | Vanillylacetone (NSC 15335) is similar in chemical structure to other spices, such as Vanillin and Eugenol, and is used as a flavor additive. Vanillylacetone (Zingerone) can reduce oxidative stress and inflammation and down-regulate NF-κB-mediated signaling pathway. Zingerone act as an anti-mitotic agent and inhibit the growth of neuroblastoma cells. |
| Target | Value |
| use | one of the main aroma components of ginger. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:47
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