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4303-67-7

4303-67-7 structure
4303-67-7 structure
  • Name: 1-Dodecylimidazole
  • Chemical Name: 1-dodecylimidazole
  • CAS Number: 4303-67-7
  • Molecular Formula: C15H28N2
  • Molecular Weight: 236.39600
  • Catalog: Signaling Pathways Anti-infection Fungal
  • Create Date: 2018-02-21 08:00:00
  • Modify Date: 2024-01-05 20:42:54
  • 1-Dodecylimidazole (N-Dodecylimidazole) is a lysosomotropic detergent and a cytotoxic agent. 1-Dodecylimidazole causes cell death by its acid-dependent accumulation in lysosomes, disruption of the lysosomal membrane, and releaseof cysteine proteases into the cytoplasm. 1-Dodecylimidazole has hypocholesterolaemic activity and broad-spectrum antifungal activity[1][2][3].
Name 1-dodecylimidazole
Synonyms Imidazole,1-dodecyl
1-n-dodecanylimidazole
1H-Imidazole,1-dodecyl
dodecylimidazole
EINECS 224-314-4
N-dodecyl imidazole
1-Laurylimidazole
1-Dodecylimidazole
1-Dodecyl-1H-imidazole
N-Laurylimidazole
Description 1-Dodecylimidazole (N-Dodecylimidazole) is a lysosomotropic detergent and a cytotoxic agent. 1-Dodecylimidazole causes cell death by its acid-dependent accumulation in lysosomes, disruption of the lysosomal membrane, and releaseof cysteine proteases into the cytoplasm. 1-Dodecylimidazole has hypocholesterolaemic activity and broad-spectrum antifungal activity[1][2][3].
Related Catalog
In Vitro N-dodecylimidazole, an acid activated detergent with a pKa of 6.3, has been shown to be cytotoxic to cells in culture. N-dodecylimidazole displayed extracellular pH (pHe)-dependent cytotoxicity against EMT-6 and MGH U1 cells. cell killing was dose dependent and was 100-fold greater at pHe 6.0 than pHe 7.0[4].
In Vivo The hypocholesterolaemic activity of 1-dodecylimidazole results in part from the inhibition of cholesterol biosynthesis at the level of 2,3-oxidosqualene sterol cyclase[2]. 1-dodecylimidazole (150 mg/kg body wt; by stomach tube; daily for 10 days) has lower serum cholesterol concentrations than control rats[2]. Animal Model: Male rats[2] Dosage: 150 mg/kg body wt Administration: By stomach tube; daily for 10 days Result: Had significantly lower serum cholesterol concentrations than untreated animals.
References

[1]. Wilson PD, et al. A relationship between multidrug resistance and growth-state dependent cytotoxicity of the lysosomotropic detergent N-dodecylimidazole. Biochem Biophys Res Commun. 1991;176(3):1377-1382.

[2]. Atkin SD, et al. The isolation of 2,3-oxidosqualene from the liver of rats treated with 1-dodecylimidazole, a novel hypocholesterolaemic agent. Biochem J. 1972;130(1):153-157.

[3]. Firestone RA, et al. Lysosomotropic agents. 7. Broad-spectrum antifungal activity of lysosomotropic detergents. J Med Chem. 1987;30(8):1519-1521.

[4]. Boyer MJ, et al. pH dependent cytotoxicity of N-dodecylimidazole: a compound that acquires detergent properties under acidic conditions. Br J Cancer. 1993;67(1):81-87.
Molecular Formula C15H28N2
Molecular Weight 236.39600
Exact Mass 236.22500
PSA 17.82000
LogP 4.80400
Storage condition 2~8℃，Seal

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NI5290000
CHEMICAL NAME :
Imidazole, 1-dodecyl-
CAS REGISTRY NUMBER :
4303-67-7
BEILSTEIN REFERENCE NO. :
0609993
LAST UPDATED :
199701
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C15-H28-N2
MOLECULAR WEIGHT :
236.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
29 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 189,69,1987
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases 37/39-26
HS Code 2933290090
288-32-4 structure

288-32-4
143-15-7 structure

143-15-7

~92%

4303-67-7 structure

4303-67-7
Literature: Kapitanov; Belousova; Shumeiko; Kostrikin; Prokop'Eva; Popov Russian Journal of Organic Chemistry, 2013 , vol. 49, # 9 p. 1291 - 1299 Zh. Org. Khim., 2013 , vol. 49, # 9 p. 1308 - 1316,9
288-32-4 structure

288-32-4
4292-19-7 structure

4292-19-7

~%

4303-67-7 structure

4303-67-7
Literature: Abate, Antonio; Petrozza, Annamaria; Cavallo, Gabriella; Lanzani, Guglielmo; Matteucci, Francesco; Bruce, Duncan W.; Houbenov, Nikolay; Metrangolo, Pierangelo; Resnati, Giuseppe Journal of Materials Chemistry A, 2013 , vol. 1, # 22 p. 6572 - 6578
288-32-4 structure

288-32-4
51323-71-8 structure

51323-71-8

~96%

4303-67-7 structure

4303-67-7
Literature: Qiao, Yunxiang; Hou, Zhenshan; Li, Huan; Hu, Yu; Feng, Bo; Wang, Xiangrui; Hua, Li; Huang, Qingfa Green Chemistry, 2009 , vol. 11, # 12 p. 1955 - 1960
288-32-4 structure

288-32-4
112-52-7 structure

112-52-7

~83%

4303-67-7 structure

4303-67-7
Literature: Savignac, A. de; Roques, C.; Hinedi, M.; Michel, G.; Lattes, A. European Journal of Medicinal Chemistry, 1990 , vol. 25, # 5 p. 449 - 454
124-22-1 structure

124-22-1

~%

4303-67-7 structure

4303-67-7
Literature: BASF Aktiengesellschaft Patent: US4450277 A1, 1984 ;
50-00-0 structure

50-00-0
124-22-1 structure

124-22-1
131543-46-9 structure

131543-46-9

~58%

4303-67-7 structure

4303-67-7
Literature: Martinez, Regina; Torregrosa, Rosario; Pastor, Isidro M.; Yus, Miguel Synthesis (Germany), 2012 , vol. 44, # 16 p. 2630 - 2638
927690-65-1 structure

927690-65-1

~%

4303-67-7 structure

4303-67-7
Literature: Liu, Xue-Feng; Dong, Li-Li; Fang, Yun Journal of Surfactants and Detergents, 2011 , vol. 14, # 4 p. 497 - 504
288-32-4 structure

288-32-4

~26%

4303-67-7 structure

4303-67-7
Literature: Abramzon; Pevzner; Kofman; Alam Russian Journal of Applied Chemistry, 1996 , vol. 69, # 12 p. 1841 - 1848
HS Code 2933290090
Summary 2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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