M1177

Myriocin

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
• 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

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: 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: dust mask type N95 (US), Eyeshields, Faceshields, Gloves