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Myriocin

Name: Myriocin
Brand: SIGMA

from Mycelia sterilia, ≥98% (HPLC), powder, immunosuppressant

Synonym(s):

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-I, Thermozymocidin

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₉NO₆

CAS Number:

35891-70-4

Molecular Weight:

401.54

UNSPSC Code:

51111800

PubChem Substance ID:

24896622

NACRES:

NA.77

MDL number:

MFCD01632772

Assay:

≥98% (HPLC)

Form:

powder

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Properties

Product Name

Myriocin from Mycelia sterilia, ≥98% (HPLC), powder

Quality Segment

200

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

methanol: 2 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O

InChI

1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1

InChI key

ZZIKIHCNFWXKDY-GNTQXERDSA-N

Description

Application

Myriocin from Mycelia sterilia has been used as an inhibitor of sphingolipid or ceramide biosynthesis in various studies.

Biochem/physiol Actions

Myriocin from Mycelia sterilia is a fungal metabolite with potent immunosuppressant activity. It inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. It disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Preparation Note

The material is readily and completely dissolved in 2 mg/ml methanol after heating at 55°C for several minutes.

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This Item	476300	46745	B0390
Sigma-Aldrich M1177 Myriocin from Mycelia sterilia	Sigma-Aldrich 476300 Myriocin, Mycelia sterilia	Supelco 46745 Spiramycin from Streptomyces sp.	Sigma-Aldrich B0390 Bilirubin Oxidase from Myrothecium verrucaria
description ≥98% (HPLC), powder	description A potent immunosuppressant.	description VETRANAL^®, analytical standard, mixture of isomers	description lyophilized powder, 15-65 units/mg protein
form powder	form solid	form -	form lyophilized powder
assay ≥98% (HPLC)	assay ≥95% (TLC)	assay -	assay -
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 200
storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C
solubility methanol: 2 mg/mL	solubility DMSO: 25 mg/mL	solubility -	solubility -
color off-white	color white	color -	color -

Pictograms

GHS06

Signal Word

Danger

Hazard Codes

H301

Precautionary Statements

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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