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R2146 Sigma-Aldrich

Radicicol from Diheterospora chlamydosporia

Green Alternative

solid

Synonym: Monorden, [1aS-(1aR*,2Z,4E,14*,15aR*)]-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione

  • CAS Number 12772-57-5

  • Empirical Formula (Hill Notation) C18H17ClO6

  • Molecular Weight 364.78

  •  MDL number MFCD06795865

  •  PubChem Substance ID 24899351

  •  NACRES NA.77

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application, Antibiotics by Mechanism of Action,
Quality Level   200
form   solid
greener alternative product score   old score: 15
new score: 9
Find out more about DOZN™ Scoring.
greener alternative product characteristics   Waste Prevention
Atom Economy
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.
color   white to yellow-white
solubility   ethanol: 10 mg/mL
Mode of action   enzyme | inhibits
antibiotic activity spectrum   fungi
greener alternative category   Re-engineered
storage temp.   −20°C
SMILES string   C[C@@H]1C[C@H]2O[C@@H]2C=C\C=C\C(=O)Cc3c(Cl)c(O)cc(O)c3C(=O)O1
InChI   1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1
InChI key   WYZWZEOGROVVHK-GTMNPGAYSA-N
Gene Information   human ... HSP90AA1(3320), SRC(6714)
rat ... Src(83805)

Description

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

Antifungal macrolactone antibiotic that inhibits protein tyrosine kinase. Radicicol induces the differentiation of HL-60 cells into macrophages, blocking cell cycle at G1 and G2. It suppresses NIH 3T3 cell transformation by diverse oncogenes such as src, ras and mos and also suppresses the expression of mitogen-inducible cyclooxygenase-2. As a cell differentiation modulator, radicicol has anti-angiogenic activity in vivo, inhibiting the proliferation of and plasminogen activator production by vascular endothelial cells.

Caution

Photosensitive

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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