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MedKoo Cat#: 318661 | Name: Riboflavin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Riboflavin, also known as vitamin B2, is an essential human nutrient that is a heat-stable and water-soluble flavin belonging to the vitamin B family.

Chemical Structure

Riboflavin
Riboflavin
CAS#83-88-5

Theoretical Analysis

MedKoo Cat#: 318661

Name: Riboflavin

CAS#: 83-88-5

Chemical Formula: C17H20N4O6

Exact Mass: 376.1383

Molecular Weight: 376.37

Elemental Analysis: C, 54.25; H, 5.36; N, 14.89; O, 25.51

Price and Availability

Size Price Availability Quantity
100g USD 350.00 2 Weeks
200g USD 550.00 2 Weeks
500g USD 950.00 2 Weeks
1kg USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Riboflavin, Vitamin B2, Vitamin G; Lactoflavin.
IUPAC/Chemical Name
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
InChi Key
AUNGANRZJHBGPY-SCRDCRAPSA-N
InChi Code
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
SMILES Code
O=C(N1)N=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=CC(C)=C(C)C=C3N=C2C1=O
Appearance
Yellow or orange crystalline powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO and water
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Riboflavin is a precursor of the coenzymes flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD). These coenzymes are of vital importance in normal tissue respiration, pyridoxine activation, tryptophan to niacin conversion, fat, carbohydrate, and protein metabolism, and glutathione reductase mediated detoxification. Riboflavin may also be involved in maintaining erythrocyte integrity. This vitamin is essential for healthy skin, nails, and hair.
In vitro activity:
In the HepG2 cell line, riboflavin deficiency induces cell apoptosis by triggering ER stress and the CHOP pathway. Riboflavin deficiency inhibited cell proliferation and caused ER stress, increased the expression of ER stress markers, increased the cell apoptosis rate, enhanced the expression of proapoptotic markers, and decreased the expression of the antiapoptotic marker. Reference: Nutrients. 2022 Aug 16;14(16):3356. https://pubmed.ncbi.nlm.nih.gov/36014863/
In vivo activity:
In an arsenic-injured rat model, it was revealed that riboflavin supplementation protected testicular structures against As2O3-induced injury via a dual inhibition of oxidative changes and a regulation of the PINK1-mediated pathway. Exposure to riboflavin led to a significant decrease of the expression levels of mitophagy related genes. Reference: Physiol Res. 2021 Aug 31;70(4):591-603. https://pubmed.ncbi.nlm.nih.gov/34062077/
Solvent mg/mL mM
Solubility
DMSO 17.9 47.45
Water 14.3 37.97
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 376.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhang B, Cao JT, Wu YB, Gao KX, Xie M, Zhou ZK, Tang J, Hou SS. Riboflavin (Vitamin B2) Deficiency Induces Apoptosis Mediated by Endoplasmic Reticulum Stress and the CHOP Pathway in HepG2 Cells. Nutrients. 2022 Aug 16;14(16):3356. doi: 10.3390/nu14163356. PMID: 36014863; PMCID: PMC9414855. 2. Long L, Pang XX, Zeng FM, Zhan XH, Xie YH, Pan F, Wang W, Liao LD, Xu XE, Li B, Wang LD, Chang ZJ, Li EM, Xu LY. Promotion of rs3746804 (p. L267P) polymorphism to intracellular SLC52A3a trafficking and riboflavin transportation in esophageal cancer cells. Amino Acids. 2021 Aug;53(8):1197-1209. doi: 10.1007/s00726-021-03025-4. Epub 2021 Jul 5. PMID: 34223992. 3. Olfati A, Tvrda E. Riboflavin recovery of spermatogenic dysfunction via a dual inhibition of oxidative changes and regulation of the PINK1-mediated pathway in arsenic-injured rat model. Physiol Res. 2021 Aug 31;70(4):591-603. doi: 10.33549/physiolres.934658. Epub 2021 Jun 1. PMID: 34062077; PMCID: PMC8820542. 4. Alhazza IM, Hassan I, Ebaid H, Al-Tamimi J, Alwasel SH. Chemopreventive effect of riboflavin on the potassium bromate-induced renal toxicity in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2020 Dec;393(12):2355-2364. doi: 10.1007/s00210-020-01938-7. Epub 2020 Jul 14. PMID: 32666286.
In vitro protocol:
1. Zhang B, Cao JT, Wu YB, Gao KX, Xie M, Zhou ZK, Tang J, Hou SS. Riboflavin (Vitamin B2) Deficiency Induces Apoptosis Mediated by Endoplasmic Reticulum Stress and the CHOP Pathway in HepG2 Cells. Nutrients. 2022 Aug 16;14(16):3356. doi: 10.3390/nu14163356. PMID: 36014863; PMCID: PMC9414855. 2. Long L, Pang XX, Zeng FM, Zhan XH, Xie YH, Pan F, Wang W, Liao LD, Xu XE, Li B, Wang LD, Chang ZJ, Li EM, Xu LY. Promotion of rs3746804 (p. L267P) polymorphism to intracellular SLC52A3a trafficking and riboflavin transportation in esophageal cancer cells. Amino Acids. 2021 Aug;53(8):1197-1209. doi: 10.1007/s00726-021-03025-4. Epub 2021 Jul 5. PMID: 34223992.
In vivo protocol:
1. Olfati A, Tvrda E. Riboflavin recovery of spermatogenic dysfunction via a dual inhibition of oxidative changes and regulation of the PINK1-mediated pathway in arsenic-injured rat model. Physiol Res. 2021 Aug 31;70(4):591-603. doi: 10.33549/physiolres.934658. Epub 2021 Jun 1. PMID: 34062077; PMCID: PMC8820542. 2. Alhazza IM, Hassan I, Ebaid H, Al-Tamimi J, Alwasel SH. Chemopreventive effect of riboflavin on the potassium bromate-induced renal toxicity in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2020 Dec;393(12):2355-2364. doi: 10.1007/s00210-020-01938-7. Epub 2020 Jul 14. PMID: 32666286.
1: Redmond RW, Kochevar IE. Medical Applications of Rose Bengal- and Riboflavin-Photosensitized Protein Crosslinking. Photochem Photobiol. 2019 Sep;95(5):1097-1115. doi: 10.1111/php.13126. Epub 2019 Jul 10. Review. PubMed PMID: 31111489. 2: Kundu B, Sarkar D, Ray N, Talukdar A. Understanding the riboflavin biosynthesis pathway for the development of antimicrobial agents. Med Res Rev. 2019 Jul;39(4):1338-1371. doi: 10.1002/med.21576. Epub 2019 Mar 29. Review. PubMed PMID: 30927319. 3: O'Callaghan B, Bosch AM, Houlden H. An update on the genetics, clinical presentation, and pathomechanisms of human riboflavin transporter deficiency. J Inherit Metab Dis. 2019 Jul;42(4):598-607. doi: 10.1002/jimd.12053. Epub 2019 Feb 21. Review. PubMed PMID: 30793323. 4: Balasubramaniam S, Christodoulou J, Rahman S. Disorders of riboflavin metabolism. J Inherit Metab Dis. 2019 Jul;42(4):608-619. doi: 10.1002/jimd.12058. Epub 2019 Mar 11. Review. PubMed PMID: 30680745. 5: Peechakara BV, Gupta M. Vitamin B2 (Riboflavin). 2019 Oct 1. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK525977/ PubMed PMID: 30247852. 6: Sepúlveda Cisternas I, Salazar JC, García-Angulo VA. Overview on the Bacterial Iron-Riboflavin Metabolic Axis. Front Microbiol. 2018 Jul 5;9:1478. doi: 10.3389/fmicb.2018.01478. eCollection 2018. Review. PubMed PMID: 30026736; PubMed Central PMCID: PMC6041382. 7: Saedisomeolia A, Ashoori M. Riboflavin in Human Health: A Review of Current Evidences. Adv Food Nutr Res. 2018;83:57-81. doi: 10.1016/bs.afnr.2017.11.002. Epub 2018 Feb 2. Review. PubMed PMID: 29477226. 8: Mahabadi N, Bhusal A, Banks SW. Riboflavin Deficiency. 2019 Jul 3. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK470460/ PubMed PMID: 29262062. 9: Naghashpour M, Jafarirad S, Amani R, Sarkaki A, Saedisomeolia A. Update on riboflavin and multiple sclerosis: a systematic review. Iran J Basic Med Sci. 2017 Sep;20(9):958-966. doi: 10.22038/IJBMS.2017.9257. Review. PubMed PMID: 29085589; PubMed Central PMCID: PMC5651462. 10: Marashly ET, Bohlega SA. Riboflavin Has Neuroprotective Potential: Focus on Parkinson's Disease and Migraine. Front Neurol. 2017 Jul 20;8:333. doi: 10.3389/fneur.2017.00333. eCollection 2017. Review. PubMed PMID: 28775706; PubMed Central PMCID: PMC5517396. 11: Yonemura S, Doane S, Keil S, Goodrich R, Pidcoke H, Cardoso M. Improving the safety of whole blood-derived transfusion products with a riboflavin-based pathogen reduction technology. Blood Transfus. 2017 Jul;15(4):357-364. doi: 10.2450/2017.0320-16. Epub 2017 May 11. Review. PubMed PMID: 28665269; PubMed Central PMCID: PMC5490732. 12: Thompson DF, Saluja HS. Prophylaxis of migraine headaches with riboflavin: A systematic review. J Clin Pharm Ther. 2017 Aug;42(4):394-403. doi: 10.1111/jcpt.12548. Epub 2017 May 8. Review. PubMed PMID: 28485121. 13: Maier P, Reinhard T. [Riboflavin UVA crosslinking in progressive keratoconus]. Ophthalmologe. 2017 Jun;114(6):571-586. doi: 10.1007/s00347-017-0500-4. Review. German. PubMed PMID: 28477073. 14: Udhayabanu T, Manole A, Rajeshwari M, Varalakshmi P, Houlden H, Ashokkumar B. Riboflavin Responsive Mitochondrial Dysfunction in Neurodegenerative Diseases. J Clin Med. 2017 May 5;6(5). pii: E52. doi: 10.3390/jcm6050052. Review. PubMed PMID: 28475111; PubMed Central PMCID: PMC5447943. 15: Chan TC, Chow VW, Jhanji V. Collagen Cross-linking With Photoactivated Riboflavin (PACK-CXL) for Bacterial Keratitis After Small Incision Lenticule Extraction (SMILE). J Refract Surg. 2017 Apr 1;33(4):278-280. doi: 10.3928/1081597X-20170126-01. Review. PubMed PMID: 28407169. 16: García-Angulo VA. Overlapping riboflavin supply pathways in bacteria. Crit Rev Microbiol. 2017 Mar;43(2):196-209. doi: 10.1080/1040841X.2016.1192578. Epub 2016 Nov 8. Review. PubMed PMID: 27822970. 17: McNulty H, Strain JJ, Hughes CF, Ward M. Riboflavin, MTHFR genotype and blood pressure: A personalized approach to prevention and treatment of hypertension. Mol Aspects Med. 2017 Feb;53:2-9. doi: 10.1016/j.mam.2016.10.002. Epub 2016 Oct 6. Review. PubMed PMID: 27720779. 18: Revuelta JL, Ledesma-Amaro R, Lozano-Martinez P, Díaz-Fernández D, Buey RM, Jiménez A. Bioproduction of riboflavin: a bright yellow history. J Ind Microbiol Biotechnol. 2017 May;44(4-5):659-665. doi: 10.1007/s10295-016-1842-7. Epub 2016 Sep 30. Review. PubMed PMID: 27696023. 19: Henriques BJ, Lucas TG, Gomes CM. Therapeutic Approaches Using Riboflavin in Mitochondrial Energy Metabolism Disorders. Curr Drug Targets. 2016;17(13):1527-34. Review. PubMed PMID: 27527619. 20: O'Brart DP. Riboflavin for corneal cross-linking. Drugs Today (Barc). 2016 Jun;52(6):331-46. doi: 10.1358/dot.2016.52.6.2494140. Review. PubMed PMID: 27458610.