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Merck

SML0406

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

別名:

2H-Pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-5-ylmethylene)-,(3E,5aS,10bR,11aS)-, Roquefortine from Penicillium roqueforti

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この商品について

実験式（ヒル表記法）:
C22H23N5O2
CAS番号:
58735-64-1
分子量:
389.45
UNSPSC Code:
12161501
NACRES:
NA.77
Assay:
≥98% (HPLC)
Quality level:
200

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SMILES string

N21C3Nc4c(cccc4)C3(CC2C(=O)N\C(=C/c5nc[nH]c5)\C1=O)C(C)(C)C=C

InChI

1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-

InChI key

SPWSUFUPTSJWNG-SXGWCWSVSA-N

biological source

Penicillium roqueforti

assay

≥98% (HPLC)

solubility

chloroform: 1 mg/mL, ethyl acetate: 1 mg/mL, DMSO: 10 mg/mL, methanol: 10 mg/mL

storage temp.

−20°C

Quality Level

200

Application

Roquefortine C has been used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC). It has also been used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC−MS/MS).

Biochem/physiol Actions

Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species.
Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. It has been found in blue cheese and in many other food products due to natural occurrence and contamination. Roquefortine C was found to be active on a wide range of organisms. It inhibits the growth of Gram-positive bacteria, and cockerels treated with roquefortine lost their righting reflex and died within 8-12 hours. Mice injected with roquefortine C experienced neurotoxic properties. Roquefortine C was also reported to inhibit cytochrome P450 as well as tubulin polymerization.

Preparation Note

Soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL) and chloroform (1 mg/mL). DMSO solution at 10 mg/mL is stable for 3 months at −20 °C.

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H373

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

target_organs

Nervous system

保管分類

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

適用法令

試験研究用途を考慮した関連法令を主に挙げております。化学物質以外については、一部の情報のみ提供しています。 製品を安全かつ合法的に使用することは、使用者の義務です。最新情報により修正される場合があります。WEBの反映には時間を要することがあるため、適宜SDSをご参照ください。

SML0406-500UG-PW: + SML0406-500UG: + SML0406-VAR: + SML0406-BULK:

jan

最新バージョンのいずれかを選択してください：

試験成績書（COA）

Lot/Batch Number
019M4132V
14171013
126M4168V
14160802
092M4103V

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Ramón O García-Rico et al.
Microbiology (Reading, England), 154(Pt 11), 3567-3578 (2008-10-30)
We have studied the role of the pga1 gene of Penicillium chrysogenum, encoding the alpha subunit of a heterotrimeric G protein, in secondary metabolite production. The dominant activating pga1(G42R) mutation caused an increase in the production of the three secondary
Thomas G Rand et al.
Toxicological sciences : an official journal of the Society of Toxicology, 87(1), 213-222 (2005-06-17)
In vitro and in vivo studies have shown that building-associated Penicillium spores and spore extracts can induce significant inflammatory responses in lung cells and animal models of lung disease. However, because spores and spore extracts comprise mixtures of bioactive constituents
T W Naudé et al.
Journal of the South African Veterinary Association, 73(4), 211-215 (2003-04-01)
Two dogs developed alarming tremorgenic nervous stimulation shortly after ingesting discarded rice that had been forgotten in a refrigerator for an undetermined period and that was covered with a grey-green mould. Both dogs exhibited vomition followed by slight salivation, tremors
Long Wang et al.
Antonie van Leeuwenhoek, 86(2), 173-179 (2004-07-29)
A unique Penicillium isolate from Chinese soil with terverticillate penicilli and ellipsoidal to cylindrical smooth-walled conidia, produces, in addition to the common metabolite ergosterol, copious amounts of an unknown peach-red pigment and the following secondary metabolites: griseofulvin, dechlorogriseofulvin, lichexanthone, roquefortine
Songul Cakmakci et al.
Journal of food protection, 75(11), 2045-2049 (2012-11-07)
Moldy Civil is a mold-ripened variety of cheese produced mainly in eastern Turkey. This cheese is produced with Civil cheese and whey curd cheese (Lor). Civil cheese has had a geographical presence since 2009 and is manufactured with skim milk.
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