D-MANNITOL DIACETONIDE
1,2:5,6-di-O-isopropylidene D-mannitol
CAS: 1707-77-3
Molecular Formula: C12H22O6
D-MANNITOL DIACETONIDE - Names and Identifiers
| Name | 1,2:5,6-di-O-isopropylidene D-mannitol |
| Synonyms | DIACETONE-D-MAN DIACETONE-D-MANNITOL Diacetone-D-Mannitol D-mannitol diacetonide D-MANNITOL DIACETONIDE 1,2,5,6-DI-Isopopylidene-D-Mannitol 1,2,5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (non-preferred name) (1S,2S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (non-preferred name) |
| CAS | 1707-77-3 |
| EINECS | 216-954-8 |
| InChI | InChI=1/C12H22O6/c1-11(2)15-5-7(17-11)9(13)10(14)8-6-16-12(3,4)18-8/h7-10,13-14H,5-6H2,1-4H3/t7-,8+,9-,10-/m1/s1 |
| InChIKey | ODYBCPSCYHAGHA-ZYUZMQFOSA-N |
D-MANNITOL DIACETONIDE - Physico-chemical Properties
| Molecular Formula | C12H22O6 |
| Molar Mass | 262.3 |
| Density | 1.175±0.06 g/cm3(Predicted) |
| Melting Point | 120-122°C(lit.) |
| Boling Point | 382.0±32.0 °C(Predicted) |
| Specific Rotation(α) | 6 º (c=5, Chloroform) |
| Flash Point | 184.8°C |
| Solubility | methanol: 100mg/mL, clear, colorless |
| Vapor Presure | 2.08E-07mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White |
| BRN | 83765 |
| pKa | 12.98±0.20(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 6.5 ° (C=8, CHCl3) |
| MDL | MFCD00003211 |
| Physical and Chemical Properties | specific rotation: 6 ° (C = 5, CHLOROFORM) |
D-MANNITOL DIACETONIDE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29329990 |
D-MANNITOL DIACETONIDE - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | diacetone-D-mannitol is white crystalline powder, melting point is 120-122 c (lit.), specific rotation is 6 (c = 5,Chloroform), boiling point is 382.0±32.0 c (Predicted), density is 1.175±0.06g/cm3(Predicted), the refractive index is 6.5 °(C = 8,CHCl3), solubility (methanol 100 mg/mL, morphology, acidity coefficient (pKa) is 12.98±0.20(Predicted), optical rotation is [α]/D 6.0±1.0 °,c = 5inchloroform. |
| application | diacetone-D-mannitol is a representative compound of polyhydroxy compounds. it is a new type of chiral selector with simple preparation and low price. it can be used to separate a variety of chiral drugs in NACE with good separation effect, but its application in actual sample separation and analysis is still rare. This is mainly due to the fact that the two enantiomers of diacetone-D-mannitol often show different pharmacodynamics, pharmacokinetics and toxicological properties. Generally speaking, the main role in clinical practice is (R)-Enantiomer,(S)-enantiomer is ineffective or has low activity, even toxic. |
| synthesis method | unsaturated ester 20 d-mannitol (19)(20g, 0.11 mol) was added to the dry acetone (200 mL) stirred solution of molten zinc chloride (30g, 0.22 mol). Continue stirring until d -mannitol is completely dissolved (22 hours), then pour the reaction mixture into the cooled K2CO3 (30g, 0.22 mol) aqueous solution (320 mL) after stirring. Filter to remove the precipitate and wash thoroughly with DCM (200 mL). The water filtrate was evaporated to remove acetone, and DCM (3 χ 200 mL) was extracted. The organic lotion and extract were washed with cold water (100 mL), dried with MgSO4, evaporated into solid residue, and recrystallized to obtain diacetone-D-mannitol 19A with white needle (18.3g, 60%) yield (18.3g, 60%). A solution of acetal 6a(210 mg,0.57 mmol) in pyrrolidine (8 mL) was heated to 90°C for 48 hours. After removing the solvent, the residue was purified by "fast" column chromatography (hexane-EtOAc) to give diacetone-D-mannose (129 mg,91%,94%). |
Last Update：2024-04-09 21:04:16
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View History
D-MANNITOL DIACETONIDE
Rubine TR
2364-75-2
Sulfurousacid, potassium salt
Cobaltic oxide monohydrate
N-DECYLZINC BROMIDE
6989-21-5
116574-14-2
HG-9-91-01
10314-98-4
Rubine TR
2364-75-2
Sulfurousacid, potassium salt
Cobaltic oxide monohydrate
N-DECYLZINC BROMIDE
6989-21-5
116574-14-2
HG-9-91-01
10314-98-4