Rose bengal | CAS#632-68-8 | Biological Stain

MedKoo Cat#: 584153 | Name: Rose bengal

Description:

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

Rose bengal is a bright bluish pink compound that has been used as a dye, biological stain, and diagnostic aid. It is commonly used in eye drops to stain damaged conjunctival and corneal cells and thereby identify damage to the eye. The stain is also used in the preparation of Foraminifera for microscopic analysis, allowing the distinction between forms that were alive or dead at the time of collection.

Chemical Structure

Rose bengal

CAS#632-68-8

Theoretical Analysis

MedKoo Cat#: 584153

Name: Rose bengal

CAS#: 632-68-8

Chemical Formula: C20H2Cl4I4K2O5

Exact Mass:

Molecular Weight: 1049.85

Elemental Analysis: C, 22.88; H, 0.19; Cl, 13.51; I, 48.35; K, 7.45; O, 7.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Rose bengal; Acid Red 94; Food Red 105; Simacid Rose Bengal

IUPAC/Chemical Name

Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium salt

InChi Key

VQHHOXOLUXRQFQ-UHFFFAOYSA-L

InChi Code

InChI=1S/C20H4Cl4I4O5.2K/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28;;/h1-2,29-30H;;/q;2*+1/p-2

SMILES Code

O=C1OC2(C3=C(OC4=C2C=C(I)C([O-])=C4I)C(I)=C([O-])C(I)=C3)C5=C1C(Cl)=C(Cl)C(Cl)=C5Cl.[K+].[K+]

Appearance

Solid 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

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,049.85 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.

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

1: Pérez-Laguna V, García-Luque I, Ballesta S, Pérez-Artiaga L, Lampaya-Pérez V, Samper S, Soria-Lozano P, Rezusta A, Gilaberte Y. Antimicrobial photodynamic activity of Rose Bengal, alone or in combination with Gentamicin, against planktonic and biofilm Staphylococcus aureus. Photodiagnosis Photodyn Ther. 2017 Nov 28. pii: S1572-1000(17)30469-6. doi: 10.1016/j.pdpdt.2017.11.012. [Epub ahead of print] PubMed PMID: 29196246. 2: Soeken TA, Zhu H, DeMartelaere S, Davies BW, Kim M, Wang HC, Aden J, Grimm R, Alt C, Kochevar IE, Johnson AJ. Sealing of Corneal Lacerations Using Photoactivated Rose Bengal Dye and Amniotic Membrane. Cornea. 2017 Nov 14. doi: 10.1097/ICO.0000000000001389. [Epub ahead of print] PubMed PMID: 29140861. 3: Wang T, Zhu L, Zhu J, Peng Y, Shen N, Yu Y, Yao M. Subacute effects of rose Bengal/Green light cross linking on rabbit thin corneal stability and safety. Lasers Surg Med. 2017 Nov 2. doi: 10.1002/lsm.22762. [Epub ahead of print] PubMed PMID: 29095506. 4: Ahmed MA, Abdelbar NM, Mohamed AA. Molecular imprinted chitosan-TiO(2) nanocomposite for the selective removal of Rose Bengal from wastewater. Int J Biol Macromol. 2017 Sep 21. pii: S0141-8130(17)32315-2. doi: 10.1016/j.ijbiomac.2017.09.082. [Epub ahead of print] PubMed PMID: 28943440. 5: Han S, Hwang BW, Jeon EY, Jung D, Lee GH, Keum DH, Kim KS, Yun SH, Cha HJ, Hahn SK. Upconversion Nanoparticles/Hyaluronate-Rose Bengal Conjugate Complex for Noninvasive Photochemical Tissue Bonding. ACS Nano. 2017 Oct 24;11(10):9979-9988. doi: 10.1021/acsnano.7b04153. Epub 2017 Sep 15. PubMed PMID: 28892611. 6: Uekubo A, Hiratsuka K, Aoki A, Takeuchi Y, Abiko Y, Izumi Y. Effect of antimicrobial photodynamic therapy using rose bengal and blue light-emitting diode on Porphyromonas gingivalis in vitro: Influence of oxygen during treatment. Laser Ther. 2016 Dec 30;25(4):299-308. doi: 10.5978/islsm.16-OR-25. PubMed PMID: 28765675; PubMed Central PMCID: PMC5532170. 7: Rosa-Pardo I, Roig-Pons M, Heredia AA, Usagre JV, Ribera A, Galian RE, Pérez-Prieto J. Fe(3)O(4)@Au@mSiO(2) as an enhancing nanoplatform for Rose Bengal photodynamic activity. Nanoscale. 2017 Jul 27;9(29):10388-10396. doi: 10.1039/c7nr00449d. PubMed PMID: 28702636. 8: Gallego-Muñoz P, Ibares-Frías L, Lorenzo E, Marcos S, Peréz-Merino P, Bekesi N, Kochevar IE, Martínez-García MC. Corneal Wound Repair After Rose Bengal and Green Light Crosslinking: Clinical and Histologic Study. Invest Ophthalmol Vis Sci. 2017 Jul 1;58(9):3471-3480. doi: 10.1167/iovs.16-21365. PubMed PMID: 28700779. 9: Amescua G, Arboleda A, Nikpoor N, Durkee H, Relhan N, Aguilar MC, Flynn HW, Miller D, Parel JM. Rose Bengal Photodynamic Antimicrobial Therapy: A Novel Treatment for Resistant Fusarium Keratitis. Cornea. 2017 Sep;36(9):1141-1144. doi: 10.1097/ICO.0000000000001265. PubMed PMID: 28691942; PubMed Central PMCID: PMC5546001. 10: Wen X, Zhang X, Szewczyk G, El-Hussein A, Huang YY, Sarna T, Hamblin MR. Potassium Iodide Potentiates Antimicrobial Photodynamic Inactivation Mediated by Rose Bengal in In Vitro and In Vivo Studies. Antimicrob Agents Chemother. 2017 Jun 27;61(7). pii: e00467-17. doi: 10.1128/AAC.00467-17. Print 2017 Jul. PubMed PMID: 28438946; PubMed Central PMCID: PMC5487662. 11: Kim S, Jo H, Jeon M, Choi MG, Hahn SK, Yun SH. Luciferase-Rose Bengal conjugates for singlet oxygen generation by bioluminescence resonance energy transfer. Chem Commun (Camb). 2017 Apr 20;53(33):4569-4572. doi: 10.1039/c7cc00041c. PubMed PMID: 28387393; PubMed Central PMCID: PMC5489260. 12: Dabrzalska M, Janaszewska A, Zablocka M, Mignani S, Majoral JP, Klajnert-Maculewicz B. Cationic Phosphorus Dendrimer Enhances Photodynamic Activity of Rose Bengal against Basal Cell Carcinoma Cell Lines. Mol Pharm. 2017 May 1;14(5):1821-1830. doi: 10.1021/acs.molpharmaceut.7b00108. Epub 2017 Apr 6. PubMed PMID: 28350966. 13: Bekesi N, Gallego-Muñoz P, Ibarés-Frías L, Perez-Merino P, Martinez-Garcia MC, Kochevar IE, Marcos S. Biomechanical Changes After In Vivo Collagen Cross-Linking With Rose Bengal-Green Light and Riboflavin-UVA. Invest Ophthalmol Vis Sci. 2017 Mar 1;58(3):1612-1620. doi: 10.1167/iovs.17-21475. PubMed PMID: 28297026. 14: Ezquerra Riega SD, Rodríguez HB, San Román E. Rose bengal in poly(2-hydroxyethyl methacrylate) thin films: self-quenching by photoactive energy traps. Methods Appl Fluoresc. 2017 Mar 9;5(1):014010. doi: 10.1088/2050-6120/aa61ae. PubMed PMID: 28276341. 15: Al-Akhras MH, Aljarrah K, Albiss B, Al-Khalili D. Influence of iron oxide nanoparticles (Fe(3)O(4)) on erythrocyte photohemolysis via photofrin and Rose Bengal sensitization. Photodiagnosis Photodyn Ther. 2017 Jun;18:111-118. doi: 10.1016/j.pdpdt.2017.02.008. Epub 2017 Feb 20. PubMed PMID: 28232076. 16: Qin J, Kunda N, Qiao G, Calata JF, Pardiwala K, Prabhakar BS, Maker AV. Colon cancer cell treatment with rose bengal generates a protective immune response via immunogenic cell death. Cell Death Dis. 2017 Feb 2;8(2):e2584. doi: 10.1038/cddis.2016.473. PubMed PMID: 28151483; PubMed Central PMCID: PMC5386459. 17: Kariminezhad H, Amani H, Khanbabaie R, Biglarnia M. Photodynamic Inactivation of E. coli PTCC 1276 Using Light Emitting Diodes: Application of Rose Bengal and Methylene Blue as Two Simple Models. Appl Biochem Biotechnol. 2017 Jul;182(3):967-977. doi: 10.1007/s12010-016-2374-3. Epub 2016 Dec 27. PubMed PMID: 28028758. 18: Santra K, Smith EA, Petrich JW, Song X. Photon Counting Data Analysis: Application of the Maximum Likelihood and Related Methods for the Determination of Lifetimes in Mixtures of Rose Bengal and Rhodamine B. J Phys Chem A. 2017 Jan 12;121(1):122-132. doi: 10.1021/acs.jpca.6b10728. Epub 2016 Dec 22. PubMed PMID: 27936713. 19: Fadlallah A, Zhu H, Arafat S, Kochevar I, Melki S, Ciolino JB. Corneal Resistance to Keratolysis After Collagen Crosslinking With Rose Bengal and Green Light. Invest Ophthalmol Vis Sci. 2016 Dec 1;57(15):6610-6614. doi: 10.1167/iovs.15-18764. PubMed PMID: 27926752. 20: Costley D, Nesbitt H, Ternan N, Dooley J, Huang YY, Hamblin MR, McHale AP, Callan JF. Sonodynamic inactivation of Gram-positive and Gram-negative bacteria using a Rose Bengal-antimicrobial peptide conjugate. Int J Antimicrob Agents. 2017 Jan;49(1):31-36. doi: 10.1016/j.ijantimicag.2016.09.034. Epub 2016 Nov 17. PubMed PMID: 27908581; PubMed Central PMCID: PMC5191983.