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I9532

Sigma-Aldrich

Icilin

≥97% (HPLC), solid

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Synonym(s):
1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetra­hydro­pyrimidin-2-one, AG-3-5
Empirical Formula (Hill Notation):
C16H13N3O4
CAS Number:
Molecular Weight:
311.29
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97% (HPLC)

form

solid

color

yellow

solubility

DMSO: 15 mg/mL

SMILES string

Oc1ccccc1N2CC=C(NC2=O)c3cccc(c3)[N+]([O-])=O

InChI

1S/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21)

InChI key

RCEFMOGVOYEGJN-UHFFFAOYSA-N

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1 of 4

This Item
I3766SML1629658403
vibrant-m

I9532

Icilin

vibrant-m

I3766

Isoliquiritigenin

vibrant-m

SML1629

Ezetimibe

vibrant-m

658403

AG 538

form

solid

form

powder

form

powder

form

solid

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

solubility

DMSO: 15 mg/mL

solubility

H2O: <0.1 mg/mL, methanol: 10 mg/mL, DMSO: 20 mg/mL

solubility

DMF: soluble ≥15 mg/mL, DMSO: soluble ≥15 mg/mL, ethanol: soluble ≥15 mg/mL, methanol: soluble ≥15 mg/mL

solubility

DMSO: 5 mg/mL

color

yellow

color

yellow to orange

color

-

color

dark orange to brown

General description

Icilin is a synthetic cooling agent and modulates human transient receptor potential cation channel (TRPA1). Icilin inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and modulates calcium release. Icilin also suppresses transient receptor potential vanilloid subtype 3 (TRPV3).

Application

Icilin has been used as cooling agent in anterior ventromedial preoptic area (VMPO) neurons.

Biochem/physiol Actions

Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol and menthol derivatives
Kuhn FJP, et al.
The Journal of Biological Chemistry, 284(7), 4102-4111 (2009)
Warm-sensitive neurons that control body temperature
Tan CL, et al.
Cell, 167(1), 47-59 (2016)
Supercooling agent icilin blocks a warmth-sensing ion channel TRPV3
Sherkheli MA, et al.
TheScientificWorldJournal, 2012(6), 859-869 (2012)
Dimitra Gkika et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(6), 7483-7499 (2020-04-12)
Recent studies have revealed gender differences in cold perception, and pointed to a possible direct action of testosterone (TST) on the cold-activated TRPM8 (Transient Receptor Potential Melastatin Member 8) channel. However, the mechanisms by which TST influences TRPM8-mediated sensory functions
Chong Wang et al.
Journal of cellular and molecular medicine (2020-12-09)
In this study, we investigated the ability of the Polysaccharide from the Eggs of Strongylocentrotus nudus (SEP) to regulate cellular autophagy and apoptosis in leukaemia cells. Human acute myeloid leukaemia (AML) cells (HL60) and murine AML cells (L1210) treated with

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