D-Isoascorbic acid supplier

Name
D-Isoascorbic acid
EINECS 201-928-0
CAS No. 89-65-6
Article Data15
CAS DataBase
Density 1.954 g/cm³
Solubility 0.1 g/mL in water
Melting Point 169-172 °C (dec.)(lit.)
Formula C₆H₈O₆
Boiling Point 552.7 °C at 760 mmHg
Molecular Weight 176.126
Flash Point 238.2 °C
Transport Information
Appearance Crystalline
Safety 26-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms D-erythro-Hexonicacid, 3-keto-, g-lactone(6CI);Erythorbic acid (7CI);Araboascorbic acid;Araboascorbic acid, D-;D-(-)-Isoascorbic acid;D-Araboascorbic acid;D-Erythorbic acid;D-arabino-Ascorbic acid;E 315;Erycorbin;Glucosaccharonic acid;Isoascorbic acid;Isovitamin C;Mercate 5;Neo-Cebicure;Saccharosonic acid;Erythorbic acid;
PSA 107.22000
LogP -1.40740

Synthetic route

: 3445-24-7
D-erythro-pentos-2-ulose

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With potassium cyanide; nitrogen; water anschl. mit wss. HCl unter Ausschluss von Luft;

: 21063-40-1
D-arabino-[2]hexulosonic acid methyl ester

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With manganese; water
With water; iron
With water; sodium hydrogencarbonate

calcium salt of/the/ D-arabino-<2>hexulosonic acid: calcium salt of/the/ D-arabino-<2>hexulosonic acid

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With ethanol; sulfuric acid anschl. mit Dicyclohexylamin und dann mit wss. NaOH;

potassium-salt of/the/ O2,O3;O4,O5-diisopropylidene-β(?)-D-arabino-<2>hexulopyranosonic acid: potassium-salt of/the/ O2,O3;O4,O5-diisopropylidene-β(?)-D-arabino-<2>hexulopyranosonic acid

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With methanol; sulfuric acid; water

sodium-salt of/the/ D-arabino-<2>hexulosonic acid: sodium-salt of/the/ D-arabino-<2>hexulosonic acid

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With methanol; sulfuric acid anschl. mit wss. NaHCO3;
With methanol; sulfuric acid anschl. mit wss. Na2CO3;

: 67-56-1
methanol

: 109-89-7
diethylamine

2-keto-D-gluconic acid methyl ester: 2-keto-D-gluconic acid methyl ester

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
at 70℃;

...Expand

: 67-56-1
methanol

: 17344-99-9
AlaOEt

2-keto-D-gluconic acid methyl ester: 2-keto-D-gluconic acid methyl ester

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
at 70℃;

...Expand

: 7647-01-0
hydrogenchloride

: 669-90-9
fructonic acid

: 7732-18-5
water

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
at 60℃; Rate constant; und 70grad;

...Expand

: 17344-99-9
AlaOEt

: 7732-18-5
water

2-keto-D-gluconic acid methyl ester: 2-keto-D-gluconic acid methyl ester

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
at 70℃;

...Expand

: 5959-82-0
D-erythro-2,3-hexodiulosono-1,4-lactone

: 89-65-6
isoascorbic acid

Conditions

Conditions	Yield
With ascorbic acid In phosphate buffer at 20℃; for 24h; pH=7.4; Product distribution; Reduction;

: 77-76-9
2,2-dimethoxy-propane

: 89-65-6
isoascorbic acid

: 50271-42-6
5,6-O-isopropylidene-D-isoascorbic acid

Conditions

Conditions	Yield
With tin(ll) chloride In acetone for 0.5h; Heating;	100%
With (1S)-10-camphorsulfonic acid In acetone at 20℃; for 1h;	98%
With hydrogenchloride In acetone Ambient temperature;	90%
With tin(ll) chloride In acetone Reflux;

: 67-64-1
acetone

: 89-65-6
isoascorbic acid

: 50271-42-6
5,6-O-isopropylidene-D-isoascorbic acid

Conditions

Conditions	Yield
With Amberlite IR-120 for 2h; Heating;	100%
With acetyl chloride at 40℃; for 4h;	83%
With copper(II) sulfate for 48h; Ambient temperature;

: 933-40-4
cycloxexanone dimethyl ketal

: 89-65-6
isoascorbic acid

: 97627-84-4
5,6-O-Cyclohexylidene-D-isoascorbic acid

Conditions

Conditions	Yield
With tin(ll) chloride In ethyl acetate for 0.5h; Heating;	99%

: 89-65-6
isoascorbic acid

: 74352-43-5
6-Bromo-6-deoxy-D-isoascorbic acid

Conditions

Conditions	Yield
With hydrogen bromide In acetic acid at 22℃; for 24h;	99%
With hydrogen bromide; acetic acid at 20℃; for 16h; Darkness;	84%
Multi-step reaction with 2 steps 1: HBr / 20 °C 2: H2O; HBr; AcOH / 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen bromide 2: deacetylation View Scheme

: 89-65-6
isoascorbic acid

: 15667-21-7
D-erythronolactone

Conditions

Conditions	Yield
Stage #1: isoascorbic acid With dihydrogen peroxide; sodium carbonate In water at 0℃; Stage #2: In water at 75℃; for 0.5h; Stage #3: With hydrogenchloride In water	91%
With dihydrogen peroxide
With dihydrogen peroxide; sodium carbonate In water at 0 - 40℃; for 2h;

: 95-54-5
1,2-diamino-benzene

: 100-63-0
phenylhydrazine

: 89-65-6
isoascorbic acid

: 68667-54-9
3-(1-phenylhydrazono-D-erythro-2,3,4-trihydroxybut-1-yl)quinoxalin-2-one

Conditions

Conditions	Yield
With acetic acid In ethanol; water for 0.0666667h; microwave irradiation;	86%

...Expand

: 89-65-6
isoascorbic acid

: 26301-79-1
D-mannono-1,4-lactone

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water under 2585.74 Torr;	82%
With hydrogen; palladium on activated charcoal In water at 50℃; under 2585.7 Torr; for 6h;	71%
With hydrogen; palladium on activated charcoal In water under 3102.9 Torr; for 288h; Ambient temperature;	51%

: 25636-49-1
3,3-dimethoxypentane

: 89-65-6
isoascorbic acid

: (5R)-5-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyfuran-2(5H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	79%

: 143-07-7
lauric acid

: 89-65-6
isoascorbic acid

: 71623-60-4
erythorbyl laurate

Conditions

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; Enzymatic reaction;	78.5%
With sulfuric acid

: 24856-58-4
1,1-dimethoxy-1-(4-bromophenyl)methane

: 75-03-6
ethyl iodide

: 89-65-6
isoascorbic acid

: (2R,4'R)-ethyl 2-[2'-(p-bromophenyl)-1',3'-dioxolan-4'-yl]-2-hydroxy ethanoate

Conditions

Conditions	Yield
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane; isoascorbic acid With trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; for 120h; Inert atmosphere; Stage #2: With dihydrogen peroxide; potassium carbonate In water at 0 - 20℃; for 16h; Stage #3: ethyl iodide In acetonitrile for 20h; Reflux;	75%

...Expand

: 98-88-4
benzoyl chloride

: 89-65-6
isoascorbic acid

: 53176-87-7
2′,3′-di-O-benzoyl-L-erythronolactone

Conditions

Conditions	Yield
Stage #1: isoascorbic acid With dihydrogen peroxide; sodium carbonate In water at 0 - 75℃; for 1h; Inert atmosphere; Stage #2: benzoyl chloride With pyridine at 0 - 20℃; for 12h; Inert atmosphere;	69%

: 89-65-6
isoascorbic acid

A: 62-76-0
sodium oxalate

B: 15667-21-7
D-erythronolactone

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium carbonate 1) 17 deg C, 5 min; 2) 40 deg C, 30 min;	A n/a B 67.5%

: 123-73-9
trans-Crotonaldehyde

: 89-65-6
isoascorbic acid

: (3R,3aR)Tetrahydro-3'-methyl-3,5',6-trihydroxy-furan-2'-spiro-5a-hexahydro-furo<3',2':2,3>furan-5-on

Conditions

Conditions	Yield
In water Ambient temperature;	65%

: p-toluenediazonium hydrogen sulfate

: 89-65-6
isoascorbic acid

: 7152-74-1
(-)-(3R-cis)-mono(tetrahydro-4-hydroxy-2-oxo-3-furanyl)ester 2-(4-methyl-phenyl)hidrazide of ethanedioic acid

Conditions

Conditions	Yield
at 0℃;	55%

: dodecandioic acid divinyl ester

: 89-65-6
isoascorbic acid

: 6-O-[(-)-D-isoascorbic acid]-6'-O-[(-)-D-isoascorbic acid] dodecanedioate

Conditions

Conditions	Yield
With immobilized lipase from Candida Antarctica In acetone at 45℃; for 16h; Molecular sieve;	49%

: 1334953-93-3
6-O-[(+)-L-ascorbic acid]-vinyl dodecanedioate

: 89-65-6
isoascorbic acid

: 6-O-[(+)-L-ascorbic acid]-6'-O-[(-)-D-isoascorbic acid] dodecanedioate

Conditions

Conditions	Yield
With immobilized lipase from Candida Antarctica In acetone at 45℃; for 16h; Molecular sieve;	47%

: 107-02-8
acrolein

: 89-65-6
isoascorbic acid

: (3S,3aR)-Tetrahydro-3,5',6-trihydroxy-furan-2'-spiro-5a-hexahydro-furo<3',2':2,3>furan-5-on

Conditions

Conditions	Yield
In water Ambient temperature;	39%

: 1576-86-9, 1576-87-0, 764-39-6
2-pentenal

: 89-65-6
isoascorbic acid

: (3R,3aR)Hexahydro-9-ethyl-3,5a,8-trihydroxy-2H,5H-furo<3',2':2,3>furo<3,4-b>pyran-5-on

Conditions

Conditions	Yield
In water Ambient temperature;	20%

: 186581-53-3, 908094-01-9
diazomethane

: 89-65-6
isoascorbic acid

: 13443-57-7, 139164-18-4
D-erythro-2,4,5,6-tetrahydro-3-methoxy-hex-2c-enoic acid-4-lactone

Conditions

Conditions	Yield
With methanol; diethyl ether at -10℃;

: 186581-53-3, 908094-01-9
diazomethane

: 89-65-6
isoascorbic acid

: 40613-68-1
D-erythro-4,5,6-trihydroxy-2,3-dimethoxy-hex-2c-enoic acid-4-lactone

Conditions

Conditions	Yield
With methanol; diethyl ether

: 544-63-8
n-tetradecanoic acid

: 89-65-6
isoascorbic acid

: 71623-58-0
erythorbyl myristate

Conditions

Conditions	Yield
With sulfuric acid
With Novozym 435 In neat (no solvent) for 72h; Inert atmosphere; Enzymatic reaction;

: 57-10-3
1-hexadecylcarboxylic acid

: 89-65-6
isoascorbic acid

: 47635-02-9
6-O-palmitoyl-L-ascorbic acid

Conditions

Conditions	Yield
With sulfuric acid

: 57-11-4
stearic acid

: 89-65-6
isoascorbic acid

: 71623-59-1
D-erythro-2,3,4,5-tetrahydroxy-6-stearoyloxy-hex-2c-enoic acid-4-lactone

Conditions

Conditions	Yield
With sulfuric acid

: 119-26-6
(2,4-dinitro-phenyl)-hydrazine

: 89-65-6
isoascorbic acid

: 35923-30-9
D-erythro-2,3-bis-(2,4-dinitro-phenylhydrazono)-4,5,6-trihydroxy-hexanoic acid-4-lactone

Conditions

Conditions	Yield
With hydrogenchloride; iodine

: 89-65-6
isoascorbic acid

: 26094-91-7
L-arabo-ascorbic acid

: 1129294-89-8
isoascorbic acid

: 89-65-6
isoascorbic acid

: 5959-82-0
D-erythro-2,3-hexodiulosono-1,4-lactone

Conditions

Conditions	Yield
With H(1+)*Fe(CN)6(3-)=HFe(CN)6(2-) In water at 20℃; Rate constant; Mechanism; further oxidants: Fe(3+)aq., Fe(OH)(2+)aq.;
With ammonium molybdate; water; dihydrogen peroxide
With p-benzoquinone In ethanol for 90h; Ambient temperature;
With iodine In ethanol; water

: 67-56-1
methanol

: 89-65-6
isoascorbic acid

A: 75795-84-5, 75829-07-1, 78512-72-8, 116499-89-9
(3S,3aS,6R,6aR)-3,3a,6-Trihydroxy-3-methoxy-tetrahydro-furo[3,2-b]furan-2-one

B: 75795-84-5, 75829-07-1, 78512-72-8, 116499-89-9
(3R,3aS,6R,6aR)-3,3a,6-Trihydroxy-3-methoxy-tetrahydro-furo[3,2-b]furan-2-one

Conditions

Conditions	Yield
With p-benzoquinone 1.) DMF, room temp.; Multistep reaction;

...Expand

: 123-73-9
trans-Crotonaldehyde

: 89-65-6
isoascorbic acid

A: (3R,3aR)Tetrahydro-3'-methyl-3,5',6-trihydroxy-furan-2'-spiro-5a-hexahydro-furo<3',2':2,3>furan-5-on

B: (3R,3aR)-3,5a,8-Trihydroxy-6-methyl-hexahydro-1,4,9-trioxa-cyclopenta[c]inden-5-one

C: (6R,6aR)-3-(3,3-Dihydroxy-1-methyl-propyl)-3,3a,6-trihydroxy-tetrahydro-furo[3,2-b]furan-2-one

Conditions

Conditions	Yield
In dimethylsulfoxide-d6 for 2h; Product distribution; other time and solvent;	A 48 % Spectr. B 31 % Spectr. C 21 % Spectr.
In perdeuteriopyridine for 0.05h;	A 45 % Spectr. B 45 % Spectr. C 10 % Spectr.

...Expand

D-Isoascorbic acid Chemical Properties

Molecular Structure of D-Isoascorbic acid (CAS NO.89-65-6):

IUPAC Name: 2-(1,2-dihydroxyethyl)-4,5-dihydroxyfuran-3-one
Empirical Formula: C₆H₈O₆
Molecular Weight: 176.1241
EINECS: 201-928-0
Melting point: 169-172 ^°C (dec.)(lit.)
Boiling Point: 552.7 °C at 760 mmHg
Flash Point: 238.2 °C
Index of Refraction: 1.711
Molar Refractivity: 35.26 cm³
Molar Volume: 90.1 cm³
Polarizability: 13.97 10 ^-24 cm³
Surface Tension: 140.5 dyne/cm
Density: 1.954 g/cm³
Enthalpy of Vaporization: 95.78 kJ/mol
Vapour Pressure: 1.62E-14 mmHg at 25°C
alpha: -17.25^o (c=10, H₂O 25 ^oC)
Storage temp: Store at 0-5^°C
Water Solubility: 1g/10mL
Appearance: Crystalline
Merck: 14,5126
Stability: Stable. Combustible. Incompatible with chemically active metals, aluminium, zinc, copper, magnesium, strong bases, strong oxidizing agents.
Product Categories: Food and Feed Additive; Sugar Acids; Vitamin Derivatives; Biochemistry;Sugars; Vitamins; Water Ttreatment Chemicals

D-Isoascorbic acid Toxicity Data With Reference

1.		mma-sat 50 mg/plate		FCTOD7 Food and Chemical Toxicology. 22 (1984),623.
2.		dnd-uns:lyms 5 mmol/L		JNSVA5 Journal of Nutritional Science and Vitaminology. 21 (1975),237.

D-Isoascorbic acid Consensus Reports

Reported in EPA TSCA Inventory.

D-Isoascorbic acid Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes of D-Isoascorbic acid (CAS NO.89-65-6): Irritant Xi
Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
24/25: Avoid contact with skin and eyes
WGK Germany: 2
RTECS: KF3015000

D-Isoascorbic acid Specification

D-Isoascorbic acid , with CAS number of 89-65-6, can be called D-erythro-Hexonicacid, 3-keto-, g-lactone(6CI) ; Araboascorbic acid ; Araboascorbic acid, D- ; D-(-)-Isoascorbic acid ; D-Araboascorbic acid ; D-Erythorbic acid ; Glucosaccharonic acid ; Saccharosonic acid .

Product Name

D-Isoascorbic acid

Synthetic route

D-Isoascorbic acid Chemical Properties

D-Isoascorbic acid Toxicity Data With Reference

D-Isoascorbic acid Consensus Reports

D-Isoascorbic acid Safety Profile

D-Isoascorbic acid Specification

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