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| CAS No.: | 15042-01-0 |
|---|---|
| Name: | (+)-5,6-O-Isopropylidene-L-ascorbic acid |
| Article Data: | 112 |
| Molecular Structure: | |
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| Formula: | C9H12O6 |
| Molecular Weight: | 216.191 |
| Synonyms: | (5R)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxyfuran-2(5H)-one;(5R)-5-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyfuran-2(5H)-one;5,6-O,O-isopropylidene-L-ascorbic acid; |
| Density: | 1.518 g/cm3 |
| Melting Point: | 217 °C (dec.) |
| Boiling Point: | 395.216 °C at 760 mmHg |
| Flash Point: | 160.964 °C |
| Appearance: | White powder |
| Safety: | 22-24/25 |
| PSA: | 85.22000 |
| LogP: | 0.39090 |
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| Conditions | Yield |
|---|---|
| With Amberlite IR-120 for 2h; Heating; | 100% |
| With acetyl chloride at 7 - 20℃; for 11h; | 100% |
| With acetyl chloride at 40℃; for 2h; | 95% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; acetone for 1h; | 100% |
| With toluene-4-sulfonic acid In acetone | 100% |
| With hydrogenchloride In acetone for 1h; | 96.7% |
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In dimethyl sulfoxide; acetone at 50℃; for 5h; | 95% |
| Conditions | Yield |
|---|---|
| In acetone at 5 - 20℃; for 22.5h; Inert atmosphere; | 91% |
| In potassium hydroxide; acetone | 77% |
| In acetone | |
| In acetone at 20℃; for 16h; | |
| In acetone |
- 50-81-7
ascorbic acid
- 15042-01-0
5,6-O-isopropylidene-L-ascorbic acid
| Conditions | Yield |
|---|---|
| With trichlorophosphate In acetone at 20℃; for 4h; | 89% |
| With copper(II) sulfate; acetone | |
| In acetone |
| Conditions | Yield |
|---|---|
| With triethylamine In 1,4-dioxane |
- 216872-53-6
3,5-O-benzylidene-6-O-t-butyldimethylsilyl-L-xylo-hex-2-ulosonic acid 1,4-lactone 2-hydrate
- 15042-01-0
5,6-O-isopropylidene-L-ascorbic acid
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aq. HOAc / 4 h / 80 °C 2: AcCl / 2 h / 18 °C View Scheme |
| Conditions | Yield |
|---|---|
| In ethyl acetate; acetone |
- 50-81-7
ascorbic acid
B
- 15042-01-0
5,6-O-isopropylidene-L-ascorbic acid
| Conditions | Yield |
|---|---|
| In acetone |
| Conditions | Yield |
|---|---|
| With acetyl chloride at 40℃; for 3h; |
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Specification
The CAS registry number of L-Ascorbicacid, 5,6-O-(1-methylethylidene)- is 15042-01-0. The systematic name is 5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyfuran-2(5H)-one. In addition, the molecular formula is C9H12O6 and the molecular weight is 216.19. It is a kind of white powder and belongs to the classes of Vitamins and Derivatives; 13C & 2H Sugars; Biochemistry; O-Substituted Sugars; Sugar Acids; Sugars; Vitamin Derivatives; Vitamins; Carbohydrates & Derivatives.
Physical properties about this chemical are: (1)ACD/LogP: -1.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 85.22 Å2; (13)Index of Refraction: 1.58; (14)Molar Refractivity: 47.37 cm3; (15)Molar Volume: 142.376 cm3; (16)Surface Tension: 64.818 dyne/cm; (17)Density: 1.518 g/cm3; (18)Flash Point: 160.964 °C; (19)Enthalpy of Vaporization: 74.608 kJ/mol; (20)Boiling Point: 395.216 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C; (22)Polarizability: 18.779 ×10-24cm3.
Preparation of L-Ascorbicacid, 5,6-O-(1-methylethylidene)- :this chemical can be prepared by 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one. This reaction will need reagent H2, catalyst Pd(OH)2 on C and solvent ethanol. The yield is about 80% with reaction pressure of 760 Pa.
![L-Ascorbicacid, 5,6-O-(1-methylethylidene)- can be prepared by 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one.](/UserFilesUpload/Preparation of L-Ascorbicacid, 5,6-O-(1-methylethylidene)-(1).jpg)
Uses of L-Ascorbicacid, 5,6-O-(1-methylethylidene)-: it can react with 1,2-bis-bromomethyl-benzene to produce 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one. This reaction will need reagent sodium hydride and solvent tetrahydrofuran. The reaction time is 30 minutes with ambient temperature. The yield is about 62%.
![L-Ascorbicacid, 5,6-O-(1-methylethylidene)- can react with 1,2-bis-bromomethyl-benzene to produce 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one](/UserFilesUpload/Uses of L-Ascorbicacid, 5,6-O-(1-methylethylidene)-.jpg)
When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. In addition, you should not breathe dust.
You can still convert the following datas into molecular structure:
(1) SMILES: O\C2=C(/O)C(=O)O[C@@H]2[C@H]1OC(C)(C)OC1
(2) InChI: InChI=1/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
(3) InChIKey: POXUQBFHDHCZAD-MHTLYPKNBS