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

HCID 6759
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
83-88-5
Standard SMILES
Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@@H](O)[C@@H](O)[C@@H](O)CO)c2cc1C
InChIKey
AUNGANRZJHBGPY-MBNYWOFBSA-N
Molecular formula
C17H20N4O6
Average molar mass
376.4 g/mol
Monoisotopic mass
376.13828437

Overview

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

Names & identifiers

Preferred name
7,8-dimethyl-10-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4(3H,10H)-dione
IUPAC
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
English name
Riboflavin
Molecular formula
C17H20N4O6
Molecular weight
376.36

Names & synonyms

7,8-dimethyl-10-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione7,8-dimethyl-10-[(2r,3r,4s)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4(3h,10h)-dione7,8-dimethyl-10-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4(3H,10H)-dioneRefChem:10742751195174-65-2C17H20N4O6Riboflavin (B2)SR-05000001670CAS-83-88-5Riboflavin, USP gradeRiboflavin Impurity 33Spectrum2_000660
Show more names
VITAMIN B2RIBOFLAVINE(-)-RiboflavinFlavaxinRiboflavin UniversalRiboflavin Vitamin B2VIT B2Riboflavin CRSVitamin B2 (Riboflavine)
SCHEMBL7707BSPBio_00226491386-80-0SPECTRUM1505347SPBio_000699SCHEMBL29456492CHEBI:95299HMS1922F06

Properties

Computed structural properties

XLogP
-1.5
Topological polar surface area
155 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
7
Rotatable bonds
5
Heavy atoms
27
Formal charge
0
Complexity
680

Physicochemical properties

Melting point
290 °C · 290 °C (dec.)(lit.)
alpha
-135 · -135 º (c=5, 0.05 M NaOH)
Boiling point
504.93 °C · 504.93°C (rough estimate)
Density
1.2112 · 1.2112 (rough estimate)
bulk density
100 kg/m3 · 100kg/m3
refractive index
-135 ° · -135 ° (C=0.5, JP Method)
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
Very slightly soluble in water, practically insoluble in ethanol (96 per cent). Solutions deteriorate on exposure to light, especially in the presence of alkali. It shows polymorphism (5.9).
form
Powder
pka
1.7 · 1.7(at 25℃)
color
Yellow to orange
PH
5.5 · 5.5-7.2 (0.07g/l, H2O, 20°C)
Odor
Slight odour
PH Range
6 · 6

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
8-10-21
PPE
Eyeshields, Gloves, type N95 (US)
wgk
1
tsca
TSCA listed
rtecs
VJ1400000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29362300
Toxicity
LD50 in rats (g/kg): >10 orally, 5.0 s.c., 0.56 i.p. (Unna, Greslin)
risk_code
11-23/24/25-39/23/24/25
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08
hazard_code
F,T
safety_code
24/25-45-36/37-16
Storage Class
11 - Combustible Solids
Hazard statements
H226-H301+H311+H331-H370
REACH Registrations
Active
Precautionary statements
P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazardous Substances Data
83-88-5(Hazardous Substances Data)

Chemistry & industry

Applications · 7 items

DescriptionA water-soluble B fraction was found in the 1920s to contain a yellow, fluorescent growth factor called riboflavin in England and vitamin G in the United States. In the early 1930s, several groups found the coenzyme forms of riboflavin 50-phosphate (flavin mononucleotide) and the further conjugate with adenylic acid (flavin adenine dinucleotide).

Occurrence(-)-Riboflavin is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

UsesVitamin B2 (riboflavin) is produced by yeast from glucose, urea, and mineral salts in an aerobic fermentation.

UsesNutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

Usesriboflavin (Vitamin B2) is used in skin care preparations as an emollient. It can be found in sun care products as a suntan enhancer. Medicinally, it is used for the treatment of skin lesions.

UsesRiboflavin is the water-soluble vitamin b2 required for healthy skin and the building and maintaining of body tissues. it is a yellow to orange-yellow crystalline powder. it acts as a coenzyme and carrier of hydrogen. it is stable to heat but may dissolve and be lost in cooking water. it is relatively stable to storage. sources include leafy vegetables, cheese, eggs, and milk.

General DescriptionThe conflicting results were eventually found to be due,in part, to deficiencies in study animals not just of vitamin B2,but also vitamin B3 (niacin), the cause of human forms of pellagra,and/or vitamin B6 (pyridoxine), another cause of dermatitis.Likewise, treatments with vitamin B2 were inconsistentbecause the early sources of this vitamin contained otherB vitamins. Vitamin B2 was eventually isolated from eggwhites in 1933 and produced synthetically in 1935. Thename riboflavine was officially accepted in 1960; althoughthe term was in common use before then. In 1966, IUPACchanged it to riboflavin, which is in common use today.Riboflavin is synthesized by all green plants and by mostbacteria and fungi. Therefore, riboflavin is found, at least insmall amounts, in most foods. Foods that are naturally highin riboflavin include milk and other dairy products, meat,eggs, fatty fish, and dark green vegetables. Chemically, riboflavin is an N-glycoside of flavin, alsoknown as lumichrome, and the sugar, ribitol .Flavin is derived from the Latin word flavus for “yellow”because of the yellow color of its crystals and yellow fluorescenceunder UV light. Riboflavin is heat stable but easilydegraded by light. Its systematic names are 7,8-dimethyl-10-ribitylisoalloxazine and 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
83-88-5
PubChem CID
6759
ChEBI
CHEBI:95299
biological source
synthetic
optical activity
-135 to · [α]/D -135.0 to -155.0°, c =0.5% in 0.05 M NaOH (dry basis)
Water Solubility
0.07 g/L · 0.07 g/L (20 ºC)
Sensitive
Light Sensitive
ex/em
443 · λex 443, 353 nm; λem 531 nm in EtOH
Merck
14 · 14,8200
BRN
97825 · 97825
BCS Class
1 · 1
Stability
Stable, but light-sensitive. Incompatible with strong oxidizing agents, reducing agents, bases, calcium, metallic salts. May be moisture sensitive.
Cosmetics Ingredients Functions
SKIN CONDITIONING - MISCELLANEOUSCOLORANT
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
InChIKey
AUNGANRZJHBGPY-SCRDCRAPSA-N
SMILES
CC1=C(C)C=C(N(C[C@H](O)[C@@H]([C@H](O)CO)O)C(C2=N3)=NC(NC2=O)=O)C3=C1
LogP
-2.009 · -2.009 (est)
SCOGS (Select Committee on GRAS Substances)
Riboflavin
CAS DataBase Reference
83 · 83-88-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
RIBOFLAVIN
FDA 21 CFR
101.9 · 101.9; 104.20; 107.10;107.100; 136.115; 137.165;137.185; 184.1695; 310.545;582.5695; 73.450
EWG's Food Scores
1 · 1
FDA UNII
2976 OFR · TLM2976OFR
NCI Dictionary of Cancer Terms
2 · riboflavin; vitamin B2
NCI Drug Dictionary
riboflavin
ATC code
1 XA26 · S01XA26
NIST Chemistry Reference
Riboflavine(83-88-5)
EPA Substance Registry System
Riboflavin (83-88-5)
UNSPSC Code
41116107 · 41116107
NACRES
79 · NA.79
Symbol(GHS)
2 · GHS02,GHS06,GHS08
Signal word
Danger
Hazard statements
226 · H226-H301+H311+H331-H370
Precautionary statements
210 · P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
F,T
Risk Statements
11 · 11-23/24/25-39/23/24/25
Safety Statements
24 · 24/25-45-36/37-16
RIDADR
1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany
1 · 1
RTECS
1400000 · VJ1400000
F
8 · 8-10-21
TSCA
TSCA listed
HS Code
29362300 · 29362300
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
83 · 83-88-5(Hazardous Substances Data)
Toxicity
50 in · LD50 in rats (g/kg): >10 orally, 5.0 s.c., 0.56 i.p. (Unna, Greslin)
REACH Registrations
Active

Upstream & downstream products

Upstream raw materials

Barbituric acidSodium dithioniteAlloxanBone glueStarch3,4-Dimethylanilinecorn syrupFormaldehyde

Downstream products

Riboflavin, 2',3',4',5'-tetraacetateLUMICHROMERiboflavin 5'-Monophosphate Sodium Salt

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
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安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
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MedChemexpress LLC021-58955995 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
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山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
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Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
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南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
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上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
美岚实业(上海)有限公司021-58958189 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
Additional notes · 1 item

DefinitionChEBI: D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vege ables, but the richest natural source is yeast. The free form occurs 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.