FComEx: Riboflavine (PC000088)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:09 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000088

FoodDB Record

FDB012160

Chemical Information

Name

Riboflavine

Description

Riboflavin, also known as lactoflavin or vitamin B2, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. 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. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Riboflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). Riboflavin exists in all living species, ranging from bacteria to humans. Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. In humans, riboflavin is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, Riboflavin is found, on average, in the highest concentration within a few different foods, such as saffrons, saskatoon berries, and leavening agents and in a lower concentration in grape wines, hippoglossus (common halibut), and spiny lobsters. Riboflavin has also been detected, but not quantified in, several different foods, such as bog bilberries, lowbush blueberries, greenthread tea, nanking cherries, and black radish. This could make riboflavin a potential biomarker for the consumption of these foods. Riboflavin is a potentially toxic compound. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast.

CAS Number

83-88-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-Riboflavin	biospider
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 9CI	db_source
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol	ChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazine	biospider
6,7-Dimethyl-9-ribitylisoalloxazine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione	ChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine	ChEBI
7,8-Dimethyl-10-ribitylisoalloxazine	biospider
Beflavin	HMDB
Beflavine	biospider
Benzo[g]pteridine riboflavin deriv.	HMDB
e 101	HMDB
E101	db_source
Flavaxin	db_source
Flavin BB	biospider
Flaxain	biospider
Food Yellow 15	biospider
Hyre	HMDB
Isoalloxazine, 7,8-dimethyl-10-D-ribityl-	biospider
Lactobene	biospider
Lactoflavin	biospider
Lactoflavine	db_source
Ovoflavine	db_source
Ribipca	biospider
Ribocrisina	biospider
Riboderm	biospider
Riboflavin	biospider
Riboflavina	ChEBI
Riboflavinum	ChEBI
Ribosyn	biospider
Ribotone	biospider
Ribovel	biospider
Russupteridine yellow III	db_source
San yellow b	HMDB
Vitaflavine	biospider
Vitamin B2	db_source
Vitamin G	db_source
Vitasan b2	HMDB

Chemical Formula

C17H20N4O6

IUPAC name

7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

InChI Identifier

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

InChI Key

AUNGANRZJHBGPY-SCRDCRAPSA-N

Isomeric SMILES

CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

Average Molecular Weight

376.3639

Monoisotopic Molecular Weight

376.138284392

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Flavins

Alternative Parents

Substituents

Flavin
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Polyol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin (CHEBI:17015 )
Water-soluble vitamins (C00255 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-1.46	HANSCH,C ET AL. (1995)
Experimental Water Solubility	0.0847 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 280° dec.	DFC

Foods of Origin