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C6696

Sigma-Aldrich

Cercosporin from Cercospora hayii

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About This Item

Empirical Formula (Hill Notation):
C29H26O10
CAS Number:
35082-49-6
Molecular Weight:
534.51
MDL number:
MFCD00212919
UNSPSC Code:
51102829
PubChem Substance ID:
24892884
NACRES:
NA.85
Pricing and availability is not currently available.

form

solid

Quality Level

200

solubility

chloroform: 9.80- 10.20 mg/mL, clear, red to red-brown

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

COC1=C(CC(C)O)c2c3c(CC(C)O)c(OC)c(O)c4C(=O)C=C5OCOc6cc(O)c(C1=O)c2c6c5c34

InChI

1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-32,35H,5-6,9H2,1-4H3

InChI key

JWFLIMIGORGZMQ-UHFFFAOYSA-N

Application

Cercosporin (C29H26O10) is a red pigment that has been isolated from cultures of a banana pathogen [1]. It has been used to study toxin biodegredation in species such as Bacterium Xanthomonas campestris pv. Zinniae [2].

Biochem/physiol Actions

A light-induced polyketide phytotoxin reported to produce singlet oxygen when photoactivated.
Cercosporin, a polyketide phytotoxin, is activated by light and in the activated state, reacts with oxygen to produce toxic oxygen species such as singlet oxygen (O2) and superoxide (O2-). Production of reactive oxygen species leads to peroxidation of lipids in the plant cell membranes.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000243076
0000229166
0000229166
0000243076
068M4056V

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Hui-Qin Chen et al.
Microbiology (Reading, England), 153(Pt 8), 2781-2790 (2007-07-31)
Cercosporin is a non-host-selective, photoactivated polyketide toxin produced by many phytopathogenic Cercospora species, which plays a crucial role during pathogenesis on host plants. Upon illumination, cercosporin converts oxygen molecules to toxic superoxide and singlet oxygen that damage various cellular components
Multiple modes of photodynamic action by cercosporin.
P E Hartman et al.
Photochemistry and photobiology, 47(5), 699-703 (1988-05-01)
Barbara J Morgan et al.
Journal of the American Chemical Society, 131(26), 9413-9425 (2009-06-06)
The total syntheses of the PKC inhibitors (+)-calphostin D, (+)-phleichrome, cercosporin, and 10 novel perylenequinones are detailed. The highly convergent and flexible strategy developed employed an enantioselective oxidative biaryl coupling and a double cuprate epoxide opening, allowing the selective syntheses
Sabine Butzloff et al.
Cytometry. Part A : the journal of the International Society for Analytical Cytology, 81(8), 698-703 (2012-06-28)
The malaria parasite Plasmodium falciparum proliferates within human erythrocytes and is thereby exposed to a variety of reactive oxygen species (ROS) such as hydrogen peroxide, hydroxyl radical, superoxide anion, and highly reactive singlet oxygen ((1)O(2)). While most ROS are already
Tanya V Taylor et al.
Applied and environmental microbiology, 72(9), 6070-6078 (2006-09-08)
The polyketide toxin cercosporin plays a key role in pathogenesis by fungal species of the genus Cercospora. The bacterium Xanthomonas campestris pv. zinniae is able to rapidly degrade this toxin. Growth of X. campestris pv. zinniae strains in cercosporin-containing medium
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