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M1177

Sigma-Aldrich

Myriocin from Mycelia sterilia

≥98% (HPLC), powder

Synonym(s):
(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-I, Thermozymocidin
Empirical Formula (Hill Notation):
C21H39NO6
CAS Number:
Molecular Weight:
401.54
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
G3381476300R0395
assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥95% (TLC)

assay

≥95% (HPLC)

form

powder

form

powder

form

solid

form

powder

color

off-white

color

yellow to orange

color

white

color

off-white

solubility

methanol: 2 mg/mL

solubility

DMSO: soluble

solubility

DMSO: 25 mg/mL

solubility

ethanol: 2 mM, DMSO: soluble

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

300

Quality Level

100

Quality Level

300

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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