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83-88-5

Basic Information
CAS No.: 83-88-5
Name: Riboflavin
Article Data: 91
Cas Database
Molecular Structure:
Molecular Structure of 83-88-5 (Riboflavin)
Formula: C17H20N4O6
Molecular Weight: 376.369
Synonyms: Vitamin B2-Riboflavin(Vitamin B2)USP/BP/EP;VB2 (Riboflavin);(-)-Riboflavin;1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol;6,7-Dimethyl-9-ribitylisoalloxazine;Beflavin;Beflavine;Benzo[g]pteridine-2,4(3H,10H)-dione,7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-;C.I. 50900;C.I. FoodYellow 15;D-Ribitol,1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-;E101;E 101 (dye);Flavaxin;Flavin BB;Flaxain;Food Yellow 15;Hyre;Lactobene;Lactoflavin;Lactoflavine;NCI 0033298;San Yellow B;Vitaflavine;Vitamin G;Vitamin B2;
EINECS: 201-507-1
Density: 1.65 g/cm3
Melting Point: 290 °C (dec.)(lit.)
Boiling Point: 504.93°C (rough estimate)
Flash Point: 9℃
Solubility: Water solubility: 0.07 g/L (20 °C)
Appearance: Yellow to orange/yellow crystalline powder
Hazard Symbols: F,T
Risk Codes: 11-23/24/25-39/23/24/25
Safety: 24/25
Transport Information: N/A
PSA: 161.56000
LogP: -1.67520
Synthetic route
67-52-7

BARBITURIC ACID

21037-26-3

N-<3,4-dimethyl-6-(phenylazo)phenyl>-D-ribitylamine

83-88-5

riboflavin

Conditions
ConditionsYield
In acetic acid; butan-1-ol for 4h; Heating;74.2%
752-13-6

tetra-O-acetyl riboflavin

83-88-5

riboflavin

Conditions
ConditionsYield
With calcium methylate
With sodium methylate
123-91-1

1,4-dioxane

67-52-7

BARBITURIC ACID

21037-26-3

N-<3,4-dimethyl-6-(phenylazo)phenyl>-D-ribitylamine

64-19-7

acetic acid

83-88-5

riboflavin

67-52-7

BARBITURIC ACID

123128-64-3

1-(2-biphenyl-2-ylazo-4,5-dimethyl-anilino)-D-1-deoxy-ribitol

83-88-5

riboflavin

87-39-8

violuric acid

3051-94-3

3,4-dimethyl-N-ribitylaniline

83-88-5

riboflavin

Conditions
ConditionsYield
With boric acid
With propionic acid
2535-20-8

6,7-dimethyl-8-ribityllumazine

431-03-8

dimethylglyoxal

83-88-5

riboflavin

83959-96-0

4a-Hydroperoxy-7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxy-pentyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

83-88-5

riboflavin

Conditions
ConditionsYield
In water Rate constant;
132855-95-9

4a-(1-Hydroxy-ethylperoxy)-7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxy-pentyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

A

19393-68-1

1-hydroxyethylhydroperoxide

B

83-88-5

riboflavin

Conditions
ConditionsYield
In water Rate constant;
132855-96-0

4a-(2-Hydroxy-2-methyl-propylperoxy)-7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxy-pentyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

A

69515-12-4

peroxy-t-butanol

B

83-88-5

riboflavin

Conditions
ConditionsYield
In water Rate constant;
114590-52-2

lampteroflavin

83-88-5

riboflavin

Conditions
ConditionsYield
With hydrogenchloride at 60℃; for 1.33333h;
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    Vitamin B2 Commodity Name Riboflavin Flowing Particle(Vitamin B2 80%) Vitamin B2 98% CAS No 83-88-5 83-88-5 M.F. C17H20N4O6 C17H20N4O6 M.W.

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History

 Riboflavin (CAS NO.83-88-5) was originally considered to have two components, a heat-labile vitamin B1 and a heat-stable vitamin B2 . In the 1920s, it was thought to be the factor necessary for preventing pellagra. Paul Gyorgi in Heidelberg was investigating egg white injury in rats in 1923,  the curative factor for this condition was called vitamin H. Since both pellagra and vitamin H deficiency were associated with dermatitis, Gyorgi decided to test the effect of vitamin B2 on vitamin H deficiency in rat. In 1933, Kuhn, Gyorgy, and Wagner found that thiamin-free extracts of yeast, liver, or rice bran prevented the growth failure of rats fed a thiamin supplemented diet. This observation enabled them to develop a rapid chemical and bioassay to isolate the factor from egg white in 1933, they called it Ovoflavin.

Specification

The Riboflavin, with the CAS registry number 83-88-5, is also known as 7,8-Dimethyl-10-ribitylisoalloxazine; Lactoflavine; Vitamin B2.It belongs to the product categories of Vitamin Ingredients;Miscellaneous Compounds;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals. Its EINECS number is 201-507-1.This chemical's molecular formula is C17H20N4O6 and molecular weight is 376.37. What's more,Its systematic name is Riboflavin. It is nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide. And it is Stable, but light-sensitive. Incompatible with strong oxidizing agents, reducing agents, bases, calcium, metallic salts. May be moisture sensitive.when you use it, avoid contact with skin and eyes.

Physical properties about Riboflavin are:(1)ACD/LogP: 0.095; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 0.10; (4)ACD/LogD (pH 7.4): 0.09; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 26.82; (8)ACD/KOC (pH 7.4): 26.74; (9)#H bond acceptors: 10; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.733; (13)Molar Refractivity: 91.104 cm3; (14)Molar Volume: 227.51 cm3; (15)Surface Tension: 70.2760009765625 dyne/cm; (16)Density: 1.654 g/cm3;

You can still convert the following datas into molecular structure:
(1)SMILES:O=C2/N=C\1/N(c3cc(c(cc3/N=C/1C(=O)N2)C)C)C[C@H](O)[C@H](O)[C@H](O)CO;
(2)Std. InChI:InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1;
(3)Std. InChIKey:AUNGANRZJHBGPY-SCRDCRAPSA-NC;

The toxicity data of Riboflavin as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 2gm/kg (2000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 75, 1942.
rat LD50 intraperitoneal 560mg/kg (560mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 75, 1942.
rat LD50 intravenous 50mg/kg (50mg/kg)   FAO Nutrition Meetings Report Series. Vol. 46A, Pg. 20, 1969.
rat LD50 oral > 10gm/kg (10000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 75, 1942.
rat LD50 subcutaneous 5gm/kg (5000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 75, 1942.

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