Irgacure-651 | CAS#24650-42-8 | photoinitiator

MedKoo Cat#: 527930 | Name: Irgacure-651

Description:

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

Irgacure 651 is a photoinitiator to enhance the polymer degradation. It was found that the addition of the Irgacure 651 to PMMA accelerated the photooxidative degradation, particularly at the early stages of exposure. The efficiency of formation of chromophoric groups in PMMA in the presence of the Irgacure initiator was significantly greater than in pure polymer. This suggests that the free-radical products of the initiator photolysis (mainly benzoyl radicals) are able to abstract hydrogen atoms from PMMA molecules.

Chemical Structure

Irgacure-651

CAS#24650-42-8

Theoretical Analysis

MedKoo Cat#: 527930

Name: Irgacure-651

CAS#: 24650-42-8

Chemical Formula: C16H16O3

Exact Mass: 256.1099

Molecular Weight: 256.30

Elemental Analysis: C, 74.98; H, 6.29; O, 18.73

Price and Availability

Size	Price	Availability	Quantity
25g	USD 150.00	Ready to ship
50g	USD 250.00	Ready to ship

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Related CAS #

No Data

Synonym

IR 651; IRG 651; Irgacure 621; Irgacure 641; Irgacure 651; Irgacure 951; Irgacure E 651; Irgacure I 651;

IUPAC/Chemical Name

1,2-Diphenyl-2,2-dimethoxyethanone

InChi Key

KWVGIHKZDCUPEU-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H16O3/c1-18-16(19-2,14-11-7-4-8-12-14)15(17)13-9-5-3-6-10-13/h3-12H,1-2H3

SMILES Code

COC(OC)(C1=CC=CC=C1)C(C2=CC=CC=C2)=O

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C22B10B05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

oral cavity

In vitro activity:

A cultured fibroblast cell line, NIH/3T3, was exposed to the photoinitiators at varying concentrations from 0.01% (w/w) to 0.1% (w/w) with and without the presence of initiating light. The results demonstrated that at low photoinitiator concentrations (< or = 0.01% (w/w)), all of the initiator molecules were cytocompatible with the exception of CQ, Irgacure 651, and 4EDMAB which had a relative survival approximately 50% lower than a control. In the presence of low intensity initiating light (approximately 6 mWcm(-2) of 365 nm UV light and approximately 60 mWcm(-2) of 470-490 nm visible light) and initiating radicals, Darocur 2959 at concentrations < or = 0.05% (w/w) and CQ at concentrations < or = 0.01% (w/w) were the most promising cytocompatible UV and visible light initiating systems, respectively. To demonstrate the potential use of cytocompatible photoinitiating systems in cell encapsulation applications, chondrocytes were encapsulated in a photocrosslinked hydrogel using 0.05% (w/w) Darocur 2959 (cytocompatible) and 0.01% (w/w) Irgacure 651 (cyto-incompatible). After photopolymerizing for 10 minutes with approximately 8 mWcm(-2) of 365 nm light, nearly all the chondrocytes survived the process with Darocur 2959 while very few of the chondrocytes survived the process with Irgacure 651. Reference: Bryant SJ, Nuttelman CR, Anseth KS. Cytocompatibility of UV and visible light photoinitiating systems on cultured NIH/3T3 fibroblasts in vitro. J Biomater Sci Polym Ed. 2000;11(5):439-57. doi: 10.1163/156856200743805. PMID: 10896041.

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 256.30 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

Formulation protocol:

Bryant SJ, Nuttelman CR, Anseth KS. Cytocompatibility of UV and visible light photoinitiating systems on cultured NIH/3T3 fibroblasts in vitro. J Biomater Sci Polym Ed. 2000;11(5):439-57. doi: 10.1163/156856200743805. PMID: 10896041.

In vitro protocol:

In vivo protocol:

TBD

1: Shi X, Liu Y, Zhao R, Li Z. Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation. J Vis Exp. 2018 Aug 1;(138). doi: 10.3791/57356. PubMed PMID: 30124641. 2: Xu L, Wang W, Yu D. Durable flame retardant finishing of cotton fabrics with halogen-free organophosphonate by UV photoinitiated thiol-ene click chemistry. Carbohydr Polym. 2017 Sep 15;172:275-283. doi: 10.1016/j.carbpol.2017.05.054. Epub 2017 May 24. PubMed PMID: 28606535. 3: Zeng J, Liu S, Wang M, Yao S, Chen Y. The synthesis of weak acidic type hybrid monolith via thiol-ene click chemistry and its application in hydrophilic interaction chromatography. Electrophoresis. 2017 May;38(9-10):1325-1333. doi: 10.1002/elps.201600526. Epub 2017 Mar 30. PubMed PMID: 28211065. 4: Gao C, Ren J, Zhao C, Kong W, Dai Q, Chen Q, Liu C, Sun R. Xylan-based temperature/pH sensitive hydrogels for drug controlled release. Carbohydr Polym. 2016 Oct 20;151:189-197. doi: 10.1016/j.carbpol.2016.05.075. Epub 2016 May 24. PubMed PMID: 27474557. 5: Wang H, Ou J, Bai J, Liu Z, Yao Y, Chen L, Peng X, Zou H. Improving permeability and chromatographic performance of poly(pentaerythritol diacrylate monostearate) monolithic column via photo-induced thiol-acrylate polymerization. J Chromatogr A. 2016 Mar 4;1436:100-8. doi: 10.1016/j.chroma.2016.01.063. Epub 2016 Jan 30. PubMed PMID: 26852266. 6: Morizane M, Kawasaki Y, Miura T, Yagi K, Esumi S, Kitamura Y, Sendo T. Photoinitiator-Initiated Estrogenic Activity in Human Breast Cancer Cell Line MCF-7. J Toxicol Environ Health A. 2015;78(23-24):1450-60. doi: 10.1080/15287394.2015.1094431. PubMed PMID: 26692070. 7: Wang H, Ou J, Liu Z, Lin H, Peng X, Zou H. Chromatographic efficiency comparison of polyhedral oligomeric silsesquioxanes-containing hybrid monoliths via photo- and thermally-initiated free-radical polymerization in capillary liquid chromatography for small molecules. J Chromatogr A. 2015 Sep 4;1410:110-7. doi: 10.1016/j.chroma.2015.07.085. Epub 2015 Jul 28. PubMed PMID: 26233253. 8: József J, Juhász L, Illyés TZ, Csávás M, Borbás A, Somsák L. Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases. Carbohydr Res. 2015 Sep 2;413:63-9. doi: 10.1016/j.carres.2015.05.008. Epub 2015 Jun 3. PubMed PMID: 26101155. 9: Xu L, Sheybani N, Yeudall WA, Yang H. The effect of photoinitiators on intracellular AKT signaling pathway in tissue engineering application. Biomater Sci. 2015 Feb;3(2):250-5. doi: 10.1039/C4BM00245H. PubMed PMID: 25709809; PubMed Central PMCID: PMC4335638. 10: Kawasaki Y, Tsuboi C, Yagi K, Morizane M, Masaoka Y, Esumi S, Kitamura Y, Sendo T. Photoinitiators enhanced 1,2-dichloropropane-induced cytotoxicity in human normal embryonic lung fibroblasts cells in vitro. Environ Sci Pollut Res Int. 2015 Mar;22(6):4763-70. doi: 10.1007/s11356-014-3939-8. Epub 2014 Dec 12. PubMed PMID: 25501643. 11: Zhang M, Cheng Z, Zhao T, Liu M, Hu M, Li J. Synthesis, characterization, and swelling behaviors of salt-sensitive maize bran-poly(acrylic acid) superabsorbent hydrogel. J Agric Food Chem. 2014 Sep 3;62(35):8867-74. doi: 10.1021/jf5021279. Epub 2014 Aug 21. PubMed PMID: 25133321. 12: Bradley EL, Stratton JS, Leak J, Lister L, Castle L. Printing ink compounds in foods: UK survey results. Food Addit Contam Part B Surveill. 2013;6(2):73-83. doi: 10.1080/19393210.2012.725774. Epub 2012 Oct 2. PubMed PMID: 24779870. 13: Versace DL, Fouassier JP, Lalevée J. The first photochemical in situ production of Ti-based nanoparticles: a SH2 strategy using bis(cyclopentadienyl)titanium dichloride (Cp2TiCl2). Macromol Rapid Commun. 2014 Apr;35(8):821-6. doi: 10.1002/marc.201300924. Epub 2014 Feb 13. PubMed PMID: 24677582. 14: Liu P, Chen Y, Zhao C, Tian L. [Determination of ten photoinitiators in fruit juices and tea beverages by solid-phase micro-extraction coupled with gas chromatography/mass spectrometry]. Se Pu. 2013 Dec;31(12):1232-9. Chinese. PubMed PMID: 24669718. 15: Cubuk S, Kahraman MV, Yetimoğlu EK, Kenan S. Photocured thiol-ene based optical fluorescence sensor for determination of gold(III). Anal Chim Acta. 2014 Feb 17;812:215-21. doi: 10.1016/j.aca.2014.01.013. Epub 2014 Jan 13. PubMed PMID: 24491784. 16: Tyagi P, Barros M, Stansbury JW, Kompella UB. Light-activated, in situ forming gel for sustained suprachoroidal delivery of bevacizumab. Mol Pharm. 2013 Aug 5;10(8):2858-67. doi: 10.1021/mp300716t. Epub 2013 Jul 8. PubMed PMID: 23734705; PubMed Central PMCID: PMC4003910. 17: Liu P, Huang E, Chen Y. [Determination of the migration of seven photoinitiators in food packaging materials into aqueous solvent]. Se Pu. 2012 Dec;30(12):1235-40. Chinese. PubMed PMID: 23593879. 18: Weed AM, Dvornik J, Stefancin JJ, Gyapong AA, Svec F, Zajickova Z. Photopolymerized organo-silica hybrid monolithic columns: characterization of their performance in capillary liquid chromatography. J Sep Sci. 2013 Jan;36(2):270-8. doi: 10.1002/jssc.201200760. Epub 2012 Dec 4. PubMed PMID: 23212714. 19: Johnsen GF, Taxt-Lamolle SF, Haugen HJ. Wear model simulating clinical abrasion on composite filling materials. Dent Mater J. 2011;30(5):739-48. Epub 2011 Sep 23. PubMed PMID: 21946496. 20: Wang H, Duan J, Yu H, Zhao L, Liang Y, Shan Y, Zhang L, Liang Z, Zhang Y. Monoliths with immobilized zirconium ions for selective enrichment of phosphopeptides. J Sep Sci. 2011 Aug;34(16-17):2113-21. doi: 10.1002/jssc.201100168. Epub 2011 Jun 6. Erratum in: J Sep Sci. 2011 Aug;34(16-17):2369. Hongjiu, Xu [Corrected to Hongjiu, Yu]. PubMed PMID: 21648081.