pyropheophorbide a

Base Information

• Chemical Name: pyropheophorbide a
• CAS No.: 24533-72-0
• Molecular Formula: C33H34 N4 O3
• Molecular Weight: 534.658
• European Community (EC) Number: 858-748-6
• Nikkaji Number: J2.217.657I
• Wikidata: Q104993625
• Mol file: 24533-72-0.mol

Synonyms:3-Phorbinepropanoicacid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, (3S-trans)-;Pyropheophorbide a (6CI,7CI); Pyrophaeophorbid A

Chemical Property of pyropheophorbide a

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1006.359°C at 760 mmHg
• Flash Point: 562.426°C
• PSA: 110.67000
• Density: 1.259g/cm³
• LogP: 4.13980
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 534.26309096
• Heavy Atom Count: 40
• Complexity: 1660

Purity/Quality:

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

Pyropheophorbide a ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(C2=NC1=CC3=C(C4=C(CC(=C5C(C(C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)O)C)C

Technology Process of pyropheophorbide a

There total 16 articles about pyropheophorbide 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: 100.0%

methyl pyropheophorbide a (6453-67-4) → pyropheophorbide a (24533-72-0)

Guidance literature:

With hydrogenchloride; In water; at 0 - 20 ℃; Inert atmosphere; Darkness;

DOI:10.1111/php.12173

Reference yield: 90.0%

pyropheophytin a (14409-87-1) → pyropheophorbide a (24533-72-0)

Guidance literature:

In hydrogenchloride; at 0 ℃;

DOI:10.1021/jo01298a043

Reference yield: 85.0%

chlorin e6 trimethyl ester (15592-17-3,35038-32-5) → pyropheophorbide a (24533-72-0)

Guidance literature:

With potassium tert-butylate; In 2,4,6-trimethyl-pyridine; at 20 - 50 ℃; for 0.333333h;

upstream raw materials:

pheophorbide-a

bis(2-hydroxyethyl) disulfide

pyropheophytin a

methyl pyropheophorbide a

Downstream raw materials:

methyl bacteriopheophorbide-d

methyl pyropheophorbide a

Refernces

• 1、 Huber, Valerie,Sengupta, Sanchita,Wuerthner, Frank. "Structure-property relationships for self-assembled zinc chlorin light-harvesting dye aggregates". . p. 7791 - 7807. Retrieved 2008.
• 2、 Numata, Munenori,Kinoshita, Daiki,Hirose, Naoya,Kozawa, Tomohiro,Tamiaki, Hitoshi,Kikkawa, Yoshihiro,Kanesato, Masatoshi. "Controlled stacking and unstacking of peripheral chlorophyll units drives the spring-like contraction and expansion of a semi-artificial helical polymer". . p. 1592 - 1598. Retrieved 2013.
• 3、 Tamiaki, Hitoshi,Monobe, Rie,Koizumi, Shun,Miyatake, Tomohiro,Kinoshita, Yusuke. "Stereoselective reduction, methylation, and phenylation of the 13-carbonyl group in chlorophyll derivatives". . p. 677 - 682. Retrieved 2013.
• 4、 Tamiaki, Hitoshi,Monobe, Rie,Koizumi, Shun,Miyatake, Tomohiro,Kinoshita, Yusuke. "Stereoselective reduction, methylation, and phenylation of the 13-carbonyl group in chlorophyll derivatives". . p. 967 - 972. Retrieved 2013.
• 5、 Khudyaeva,Belykh,Shevchenko,Maximova,Zainullina,Vakhitova, Yu. V.,Shchukina,Buravlev,Chukicheva, I. Yu.,Kutchina. "Conjugates of natural chlorins and isobornylphenols with a different length of the spacer between the chlorin and terpenephenolic fragments: synthesis and antioxidant activity". . p. 2157 - 2164. Retrieved 2017.
• 6、 Belik, A. Yu.,Buyanovskaya, A. G.,Filatova, N. V.,Goryachev, N. S.,Klemenkova, Z. S.,Koifman, M. O.,Kotelnikov, A. I.,Romanova, V. S.,Rybkin, A. Yu.,Sadkov, A. P.,Talanova, V. N.,Terentiev, A. A.. "Nanoparticles of water-soluble dyads based on amino acid fullerene C60 derivatives and pyropheophorbide: Synthesis, photophysical properties, and photodynamic activity". . . Retrieved 2021.
• 7、 Chaturvedi, Pankaj Kumar,Kim, Yong-Wan,Kim, Sang Soo,Ahn, Woong Shick. "Phototoxic effects of pyropheophorbide-a from chlorophyll-a on cervical cancer cells". . p. 182 - 187. Retrieved 2014.
• 8、 Khadria, Anjul,De Coene, Yovan,Gawel, Przemyslaw,Roche, Cécile,Clays, Koen,Anderson, Harry L.. "Push-pull pyropheophorbides for nonlinear optical imaging". . p. 947 - 956. Retrieved 2017.
• 9、 Mal'Shakova, Marina V.,Velegzhaninov, Ilya O.,Rasova, Elena E.,Belykh, Dmitry V.. "Novel chlorophyll a derivatives with ester-linked galactose fragments for photodynamic therapy and fluorescence diagnostics of cancer". . p. 135 - 144. Retrieved 2021/01/11.