Pheophorbide A

Base Information

• Chemical Name: Pheophorbide A
• CAS No.: 15664-29-6
• Molecular Formula: C35H36N4O5
• Molecular Weight: 592.695
• Mol file: 15664-29-6.mol

Synonyms:3-Phorbinepropanoicacid, 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-,[3S-(3a,4b,21b)]-;3-Phorbinepropionic acid,21-carboxy-14-ethyl-4,8,13,18-tetramethyl-20-oxo-9-vinyl-, 21-methyl ester(8CI);Pheophorbide a (6CI,7CI);2-Deacetyl-2-vinylbacteriopheophorbide;Phaeophorbide a;Pheophorbide a5;

Chemical Property of Pheophorbide A

Chemical Property:

• Melting Point: 191-195 °C
• Boiling Point: 1018.984 °C at 760 mmHg
• Flash Point: 570.061 °C
• PSA: 136.97000
• Density: 1.282 g/cm³
• LogP: 3.53890
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble0.5mg/mL, clear (warmed)

Purity/Quality:

98%,99%, ^*data from raw suppliers

PheophorbideA(>80%)(mixtureofdiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Pheophorbide a is a chlorophyll-related compound studied for it’s anti-tumor & anti-cancer activity. Pheophorbide-a has been used as a photosensitizer: for the photodynamic therapy (PDT) in oral cancer cell linesto test its effect on inducing oxidative stress and death in L. amazonensisto test its effect on the viability of HeLa cells

Technology Process of Pheophorbide A

There total 26 articles about Pheophorbide A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

pheophytin-a → pheophorbide A (15664-29-6,78964-31-5)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1111/j.1751-1097.2007.00092.x

Reference yield: 92.0%

pheophytin a (603-17-8) → pheophorbide-a (15664-29-6)

Guidance literature:

In water; trifluoroacetic acid; at 0 ℃; for 0.916667h;

DOI:10.1021/jo01298a043

Reference yield: 90.0%

pheophytin a (603-17-8,47907-36-8,74984-11-5,74984-81-9,75598-38-8) → pheophorbide A (15664-29-6,78964-31-5)

Guidance literature:

With trifluoroacetic acid; In water; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm2005139

upstream raw materials:

pheophytin a

chlorophyll-a

chlorophyll a

pheophytin a

Downstream raw materials:

chlorin e6

chlorin e6 trimethyl ester

3¹,3²-dihydro-pheophorbide-a

pyropheophorbide a

Refernces

• 1、 Cao, Lei,Dong, Yi,Li, Guangzhe,Li, Yueqing,Wang, Liu,Zhao, Weijie. "Anti-tumor evaluation of a novel methoxyphenyl substituted chlorin photosensitizer for photodynamic therapy". . . Retrieved 2020.
• 2、 Belykh,Mal'Shakova,Yudina,Zavadskaya,Khudyaev,Kuchin. "Synthesis of potential antitumor agents, dimeric and trimeric chlorins, from methylpheophorbide a". . p. 719 - 728. Retrieved 2011.
• 3、 Otvagin, Vasilii F.,Nyuchev, Alexander V.,Kuzmina, Natalia S.,Grishin, Ivan D.,Gavryushin, Andrei E.,Romanenko, Yuliya V.,Koifman, Oscar I.,Belykh, Dmitrii V.,Peskova, Nina N.,Shilyagina, Natalia Yu,Balalaeva, Irina V.,Fedorov, Alexey Yu.. "Synthesis and biological evaluation of new water-soluble photoactive chlorin conjugate for targeted delivery". . p. 740 - 750. Retrieved 2018.
• 4、 You, Hyun,Yoon, Hyo-Eun,Yoon, Jung-Hoon,Ko, Hyojin,Kim, Yong-Chul. "Synthesis of pheophorbide-a conjugates with anticancer drugs as potential cancer diagnostic and therapeutic agents". . p. 5383 - 5391. Retrieved 2011.
• 5、 Wasielewski, Michael R.,Svec, Walter A.. "Synthesis of Covalently Linked dimeric Derivatives of Chlorophyll a, Pyrochlorophyll a, Chlorophyll b, and Bacteriochlorophyll a". . p. 1969 - 1974. Retrieved 1980.
• 6、 Meng, Zhi,Yu, Bin,Han, Guiyan,Liu, Minghui,Shan, Bin,Dong, Guoqiang,Miao, Zhenyuan,Jia, Ningyang,Tan, Zou,Li, Buhong,Zhang, Wannian,Zhu, Haiying,Sheng, Chunquan,Yao, Jianzhong. "Chlorin p6-Based Water-Soluble Amino Acid Derivatives as Potent Photosensitizers for Photodynamic Therapy". . p. 4999 - 5010. Retrieved 2016.
• 7、 Sadaoka, Kana,Shoji, Sunao,Hirota, Keiya,Tsukatani, Yusuke,Yoshitomi, Taichi,Tamiaki, Hitoshi,Kashimura, Shigenori,Saga, Yoshitaka. "Pheophytinization kinetics of chlorophyll c under weakly acidic conditions: Effects of acrylic acid residue at the 17-position". . p. 6915 - 6919. Retrieved 2013.
• 8、 Teramura, Misato,Harada, Jiro,Tamiaki, Hitoshi. "In vitro demethoxycarbonylation of various chlorophyll analogs by a BciC enzyme". . p. 163 - 171. Retrieved 2019.
• 9、 Belykh,Kopylov,Gruzdev,Kuchin. "Opening of the extra ring in pheophorbide a methyl ester by the action of amines as a one-step method for introduction of additional fragments at the periphery of chlorin macroring". . p. 577 - 585. Retrieved 2010.