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R0508

Sigma-Aldrich

(−)-Riboflavin

acrylamide photopolymerization tested

Synonym(s):

Lactoflavin, Vitamin B2, Vitamin G

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About This Item

Empirical Formula (Hill Notation):
C17H20N4O6
CAS Number:
83-88-5
Molecular Weight:
376.36
Beilstein/REAXYS Number:
97825
EC Number:
201-507-1
MDL number:
MFCD00005022
UNSPSC Code:
12352200
PubChem Substance ID:
57654584

biological source

synthetic (organic)

form

powder

mp

290 °C (dec.) (lit.)

suitability

acrylamide photopolymerization tested

foreign activity

Protease, none detected

SMILES string

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

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

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Application

Riboflavin is suitable as a photopolymerization reagent in PAGE by forming free radicals in aqueous solution in the presence of light. Riboflavin photodecomposes to leucoflavin. No free radicals are formed in the absence of oxygen but traces of oxygen allows for leucoflavin to reoxidize with free-radical generation. The catalysts TEMED or DMAPN are commonly added to speed up the free radical formation. The free radicals will cause acrylamide and bis-acrylamide to polymerize to form a gel matrix which can be used for sieving macromolecules. Riboflavin is commonly used in the stacking gel for non-denaturing PAGE because native proteins can be sensitive to persulfate ions from ammonium persulfate. Another advantage of riboflavin over ammonium persulfate is that it will not start polymerizing until the gel is illuminated.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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George D Kymionis et al.
American journal of ophthalmology, 157(1), 110-115 (2013-11-10)
To evaluate and compare the depth of the corneal stromal demarcation line after corneal collagen cross-linking (CXL) using 2 different methods: confocal microscopy and anterior segment optical coherence tomography (AS OCT). Prospective, comparative, interventional case series. Seventeen patients (18 eyes)
Zisis Gatzioufas et al.
Journal of refractive surgery (Thorofare, N.J. : 1995), 29(12), 846-848 (2013-10-31)
To investigate the effect of high-fluence corneal collagen cross-linking (CXL) with riboflavin and ultraviolet-A in the management of progressive keratoconus. Preliminary results from a prospective cohort study. Seven eyes from 7 patients with progressive keratoconus subjected to CXL were included.
Nacim Bouheraoua et al.
Investigative ophthalmology & visual science, 55(11), 7601-7609 (2014-10-30)
We compared the efficacy and early morphological changes in the cornea following conventional (C-CXL), transepithelial by iontophoresis (I-CXL), and accelerated (A-CXL) collagen cross-linking in keratoconus. A total of 45 eyes of 45 patients with progressive keratoconus who underwent corneal collagen
Bárbara J Henriques et al.
Current medicinal chemistry, 17(32), 3842-3854 (2010-09-23)
Riboflavin, commonly known as vitamin B2, is the precursor of flavin cofactors. It is present in our typical diet, and inside the cells it is metabolized to FMN and FAD. As a result of their rather unique and flexible chemical
Daniel R Cardoso et al.
Food & function, 3(5), 487-502 (2012-03-13)
Riboflavin, vitamin B₂, and flavins (as riboflavin building blocks or degradation products) are efficient photosensitizers inducing oxidative damage to light-exposed tissue and food by substrate-dependent mechanisms, for which protection is offered by specific nutrients. Phenolic and N-heterocyclic amino acids and
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