Skip to Content
Merck

C2389

Cerulenin

from Cephalosporium caerulens, ≥98% (HPLC), powder, de novo phospholipid synthesis inhibitor

Synonym(s):

Helicocerin, (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C12H17NO3
CAS Number:
17397-89-6
Molecular Weight:
223.27
NACRES:
NA.77
PubChem Substance ID:
24892323
UNSPSC Code:
51111800
EC Number:
241-424-8
MDL number:
MFCD00083595
Beilstein/REAXYS Number:
4140423
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
200

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Cerulenin, ≥98% (HPLC), from Cephalosporium caerulens

InChI key

PTNNGEBMCNMENY-JIVMHGEESA-N

InChI

1S/C13H18O3/c1-3-4-5-6-7-8-9-11(15)13-12(16-13)10(2)14/h3-4,6-7,12-13H,5,8-9H2,1-2H3/b4-3+,7-6+/t12-,13+/m0/s1

SMILES string

C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O

biological source

Cephalosporium caerulens

assay

≥98% (HPLC)

form

powder

mp

93 °C

solubility

acetone: 19.60-20.40 mg/mL, clear to slightly hazy, colorless to yellow

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

Gene Information

human ... FASN(2194)

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

Cerulenin has been used:

  • as a fatty acid synthase inhibitor to study its effects on aldosterone-induced trained immunity
  • as a blocker of fatty acid synthase to study its effects on the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV2)
  • as a supplement in yeast extract–peptone–dextrose/glycerol (YPD/G) agar plates for the isolation of cerulenin-resistant yeast strains

General description

Cerulenin, an inhibitor of de novo phospholipid synthesis triggers apoptosis in various wild type p53 and mutant p53 tumor cell lines. This fungal antibiotic also blocks the condensing enzyme involved in fatty acid and polyketide biosynthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000335526
0000335528
0000335527
0000333130
0000308046

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Sabrina Schubert et al.
Antimicrobial agents and chemotherapy, 55(5), 2212-2223 (2011-03-16)
Constitutive overexpression of the Mdr1 efflux pump is an important mechanism of acquired drug resistance in the yeast Candida albicans. The zinc cluster transcription factor Mrr1 is a central regulator of MDR1 expression, but other transcription factors have also been
Nepovirus
Sanfacon H, et al.
Encyclopedia of Virology (2008)
Darren C J Wong et al.
Frontiers in plant science, 9, 839-839 (2018-07-05)
Hundreds of orchid species secure pollination by sexually luring specific male insects as pollinators by chemical and morphological mimicry. Yet, the biochemical pathways involved in the synthesis of the insect sex pheromone-mimicking volatiles in these sexually deceptive plants remain poorly
Key role of mitochondria in cerulenin-mediated apoptosis
Heiligtag SJ, et al.
Cell Death and Differentiation (2002)
Su Gao et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 301(1), R209-R217 (2011-04-22)
Hypothalamic fatty acid metabolism is involved in central nervous system controls of feeding and energy balance. Malonyl-CoA, an intermediate of fatty acid biosynthesis, is emerging as a significant player in these processes. Notably, hypothalamic malonyl-CoA has been implicated in leptin's
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service