2-deoxy-D-arabino-hexopyranose
2-Deoxy-D-glucose
CAS: 154-17-6
Molecular Formula: C6H12O5
2-deoxy-D-arabino-hexopyranose - Names and Identifiers
| Name | 2-Deoxy-D-glucose |
| Synonyms | 2-deoxy-glucos Deoxy-d-glucose D-2-GLUCODESOSE 2-deoxy-d-glucos 2-deoxy-d-mannose 2-Deoxy-D-glucose 2-Deoxy-D-Arabino 2-desoxy-d-glucose 2-deoxyhexopyranose 2-deoxy-d-arabino-hexos 2-deoxy-D-arabino-hexose 2-deoxy-D-glucose grade ii 2-deoxy-D-glucose grade iii 2-deoxy-D-glucose sigmaultra 2-deoxy-D-arabino-hexopyranose 2-deoxy-beta-D-arabino-hexopyranose 2-deoxy-alpha-D-arabino-hexopyranose 2-deoxy-D-glucose, mixture of anomers |
| CAS | 154-17-6 |
| EINECS | 205-823-0 |
| InChI | InChI=1/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5-,6+/m1/s1 |
| InChIKey | PMMURAAUARKVCB-CEZCPVKQSA-N |
2-deoxy-D-arabino-hexopyranose - Physico-chemical Properties
| Molecular Formula | C6H12O5 |
| Molar Mass | 164.16 |
| Density | 1.1738 (rough estimate) |
| Melting Point | 146-147°C(lit.) |
| Boling Point | 211.61°C (rough estimate) |
| Specific Rotation(α) | 45.5 º (c=2, H2O) |
| Flash Point | 202.3°C |
| Water Solubility | Soluble in water. |
| Solubility | Soluble in water and ethanol. |
| Vapor Presure | 1.8E-08mmHg at 25°C |
| Appearance | White powder |
| Color | white |
| Merck | 14,2904 |
| BRN | 1723331 |
| pKa | pK1:12.52 (25°C) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day. |
| Refractive Index | 46.5 ° (C=1, H2O) |
| MDL | MFCD00151328 |
| Use | This product is for scientific research only and shall not be used for other purposes. |
2-deoxy-D-arabino-hexopyranose - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | MQ3325000 |
| FLUKA BRAND F CODES | 3-10 |
| TSCA | Yes |
| HS Code | 29400090 |
2-deoxy-D-arabino-hexopyranose - Reference
| Reference Show more | 1. Gao Qi, Han Yue, Xu Wei, et al. Anti-tumor Activity of Single Chain Antibody JZC00 Combined with 2-Deoxyglucose [J]. Journal of China Pharmaceutical University 2020 v.51(02):89-95. |
2-deoxy-D-arabino-hexopyranose - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| application | 2-deoxy-D-glucose is an inhibitor of glucose metabolism and has been reported to reverse lupus symptoms in mice together with metformin (M258815). 2-deoxy-D-glucose is a derivative of D-glucose. It is an antimetabolite and an important component of orthomyxovirus, paramyxovirus and herpes virus envelope. It can interfere with the synthesis of virus-specific glycoproteins and effectively inhibit the proliferation of herpes monovirus, RNA and DNA envelope virus, breast cancer cells, etc. Antiviral and anti-cancer drugs made of 2-deoxy-D-glucose have been used in clinical treatment research such as herpes monovirus, influenza, AIDS and cancer; anti-aging made of 2-deoxy-D-glucose Cosmetics and medical and health products are also on the market. Therefore, as a drug for the treatment of cancer, viral diseases and anti-aging, 2-deoxy-D-glucose has a wide range of application prospects and a huge market demand. |
| overview | 2-deoxy-D-glucose is an anti-metabolic substance of D-glucose, which has the effects of interfering with the synthesis of virus-specific glycoproteins, inhibiting herpes monovirus, RAN and DNA envelope virus, cancer cell proliferation, etc. At present, antiviral and anticancer drugs prepared from 2-deoxy-D-glucose have been clinically applied to herpes monovirus and cancer treatment, and health products and anti-aging cosmetics prepared from 2-deoxy-D-glucose have also been marketed. 2-DeoxyD-glucose has no toxic side effects, and has a wide range of applications in the fields of medical and health products, anti-aging cosmetics and life science research, with huge market potential and good development prospects. |
| preparation method | a, preparation of intermediates 1.08g of acetoglucosene is dissolved in 5mL of dichloromethane, the ice bath is cooled to 0 ℃ for 15 minutes, then the ice bath is removed, and 0.2mL of hydrogen bromide/acetic acid (HBr/HOAc) solution with a mass percentage concentration of 30% and 10mL of acetic anhydride are added in turn, the selective addition reaction was carried out by stirring at 22 ℃ for 24 hours. After the reaction, anhydrous sodium acetate was added to neutralize until pH = 7, stirring for 20 minutes. After filtration, the solution was swirled under reduced pressure at 25 ℃ and the pressure was 0.1MPa. The obtained solid was recrystallized with 10mL of solvent mixed with petroleum ether and ethyl acetate in a volume ratio of 1:4, then the white solid 2-deoxy-1, 3,4, 6-tetra-O-acetyl-D-glucose 1.30g was prepared by filtration and vacuum drying under reduced pressure with 99% yield. B, synthesis of 2-deoxy-D-glucose 1.0g of the prepared intermediate 2-deoxy-1, 3,4, 6-tetra-O-acetyl-D-glucose is added to 10mL of hydrochloric acid with a concentration of 37% for acid-catalyzed hydrolysis reaction, the reaction temperature is 75 ℃, the reaction time is 4 hours, and the reaction is cooled to room temperature after the end of the reaction, after removing acetyl groups, it is neutralized with 50% (w eight percent) sodium hydroxide solution to pH = 7, then the reaction solution is extracted twice with 10mL methanol solvent, and the extraction solution is combined and then swirled under reduced pressure. The swirled temperature is 28 ℃, and the pressure is 0.1MPa. The obtained solid is recrystallized with 10mL of solvent mixed with methanol and acetone in a volume ratio of 1:1.5, then, after filtration and vacuum drying, a white crystalline solid of 2-deoxy-D-glucose 0.41g was prepared with a yield of 81%. |
| use | is a natural antimetabolite antibiotic, which can inhibit virus infection, yeast fermentation, bacteria and tumor cell growth and other physiological and pharmacological effects. It has antiviral, antibacterial, anti-cancer, anti-epilepsy, anti-aging and other effects. It is used to prevent virus and pathogenic bacteria infection, etc., can prevent infectious diseases caused by HSV, HIV, influenza virus and other pathogenic bacteria, and can treat herpes, etc. It is mainly used for the prevention and treatment of various viral diseases and immunosuppressive diseases of livestock and poultry. It can also be used as an auxiliary treatment for bacterial and mycoplasma infections. It has broad application prospects in medicine and cosmetics industries. Yongzeng chemical, currently mainly used in poultry, veterinary drugs. 2-Deoxy-D-Glucose (2-Deoxy-D-Glucose,2-DG) is a natural antimetabolite antibiotic, which can inhibit virus infection, yeast fermentation, pathogenic bacteria and tumor cell growth. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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