Cercosporin
Molecular Formula
C29H26O10
M.W.
534.51
CAS number
35082-49-6
MSDS
Source
Cercospora kikuchii
Fermentek product Code
CRS-001
Brand/grade
For research
Appearance
Dark red powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
220°C-230°C
Solubility test
Clear red solution at 10mg/ml of DMSO, Clear red solution at 10mg/ml of Methanol
Names and identifiers

Synonyms:

  • Isocercosporin
  • Cercosporin

IUPAC:  5,12-Dihydroxy-8,9-bis[(2R)-2-hydroxypropyl]-7,10-dimethoxyperylo[1,12-def][1,3]dioxepine-6,11-dione 

Chemical names:

RTECS#:  N.A.

EU number
n.a.
Description

Cercosporin is a light-induced polyketide phytotoxin reported to produce singlet oxygen when photoactivated. Acts as a potent and specific PKC inhibitor. Competes for the phorbol binding site. Anticancer compound. Also displays antiproliferative; antiparasitic and antimicrobial properties. Cercosporin is a photosensitizing toxin produced by fungal plant pathogens in the genus Cercospora. Cercosporin produces singlet oxygen and superoxide when irradiated by light, and damages plants by causing a peroxidation of the membrane lipids. This membrane damage leads to a loss in membrane fluidity, leakage of nutrients, and rapid death of the plant cell. Cercosporin is toxic to mice and bacteria in addition to plants, and attempts to select plant cells in vitro for resistance to cercosporin have not been successful. A large number of fungal species, however, are resistant to cercosporin. Carotenoids and the fungal cell wall appear to play a critical role in the resistance of fungi to cercosporin.

InChl Key
MXLWQNCWIIZUQT-NFJWQWPMSA-N
Canonical SMILES
CC(CC1=C(C(=C2C(=O)C=C3C4=C5C(=CC(=O)C6=C(C(=C(C(=C56)C1=C42)CC(C)O)OC)O)OCO3)O)OC)O
Isomeric SMILES
C[C@H](CC1=C(C(=C2C(=O)C=C3C4=C5C(=CC(=O)C6=C(C(=C(C(=C56)C1=C42)CC(C)O)OC)O)OCO3)O)OC)O
Solubility ( literature )
  • Soluble in DMSO, ethanol or methanol (lit)
  • Soluble in 1mg/ml ethanol, methanol, DMSO
  • Soluble in 1mg/liter H2O
  • Melting Point: 241℃ lit - Scifinder
Compound Classification
  • Anticancer agent
  • protein kinase C inhibitor

 

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Hygroscopic substance.
Protect from moisture
Protect from light !
Open carefully.
Use the original container to store the product.
Keep the lid tightly closed.
Avoid exposing to strong direct light.
Other vendors may recommend higher temperatures for storage.
Retest time
3 Years
Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Transport safety: Not Dangerous Goods; Not Regulated
Available since
Title
MP lit
Value
241°C scifinder; 225-228℃ ; biolinks
Title
LD50 mouse interperitoneal
Value
LD50 >200 mg​/kg i.p. in mice
Title
activity
Value
anticancer agents and protein kinase C inhibitor
Title
comments CAS
Value
There are Cercosporin 35082-49-6 , Iso-Cercosporin 40501-77-7
Title
PG
Value
none. not hazardous.
Signal to sort
C