4-dimethylaminoazobenzene

パラジメチルアミノアゾベンゼン。4-ジメチルアミノアゾベンゼン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/01 15:33:40」(JST)

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Methyl yellow
IUPAC name p-Dimethylaminoazobenzene
Other names 4-Dimethylaminoazobenzene, DAB, N,N-Dimethyl-4-phenylazoaniline, N,N-Dimethyl-4-aminoazobenzene, Butter Yellow, Solvent Yellow 2, C.I. 11020
Identifiers
CAS number	60-11-7 Y
PubChem	6053
ChemSpider	5829 Y
UNII	A49L8E13FD Y
EC number	200-455-7
ChEMBL	CHEMBL263116 Y
RTECS number	BX7350000
Jmol-3D images	Image 1
SMILES N(=N/c1ccccc1)\c2ccc(N(C)C)cc2
InChI InChI=1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3/b16-15+ Y Key: JCYPECIVGRXBMO-FOCLMDBBSA-N Y InChI=1/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3/b16-15+ Key: JCYPECIVGRXBMO-FOCLMDBBBF
Properties
Molecular formula	C14H15N3
Molar mass	225.29 g mol−1
Appearance	Yellow crystals
Melting point	111–116 °C (232–241 °F; 384–389 K) decomposes
Solubility in water	13.6 mg/l
log P	4.58
Hazards
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H301, H351
GHS precautionary statements	P281, P301+310
EU classification	T
R-phrases	R25, R40
S-phrases	S36/37, S45
NFPA 704	1 2 0
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Methyl yellow, or C.I. 11020, is a chemical compound which may be used as a pH indicator.

Methyl yellow (pH indicator)
below pH 2.9		above pH 4.0
2.9	↔	4.0

In aqueous solution at low pH, methyl yellow appears red. Between pH 2.9 and 4.0, methyl yellow undergoes a transition, to become yellow above pH 4.0.

Safety

It is a possible carcinogen. As "butter yellow", the agent had been used as a food additive before its toxicity was recognized. The result from consuming such chemicals is tumors on the liver.

References

See also

Structurally similar compounds:

• Methyl red
• Oil Yellow DE

External links

• International Chemical Safety Card 1498
• "para-dimethylaminoazobenzene". Inchem. 
• CDC - NIOSH Pocket Guide to Chemical Hazards
• Chung, K. T.; Fulk, G. E.; Andrews, A. W. (1981). "Mutagenicity testing of some commonly used dyes" (pdf). Applied and Environmental Microbiology 42 (4): 641–648. PMC 244076. PMID 7039509. 

English Journal

• Effect of retinyl acetate on transglutaminase 2 activity in carcinogen treated rat liver.

• Aydin O1, Akyuz F1, Tekin N2, Ustuner M3, Degirmenci I3, Burukoglu D4, Ozden H5.
• Biotechnic & histochemistry : official publication of the Biological Stain Commission.Biotech Histochem.2016 Apr 18:1-10. [Epub ahead of print]
• Transglutaminase 2 (TG2) has been implicated in wound healing, cellular differentiation, apoptosis and cell survival. TG2 activity increases following acute and chronic liver injury; however, the role of TG2 in tumors, is controversial. TG2 is a retinoid-inducible enzyme. We investigated the effects
• PMID 27089473

• Azobenzene-aminoglycoside: Self-assembled smart amphiphilic nanostructures for drug delivery.

• Deka SR1, Yadav S2, Mahato M1, Sharma AK3.
• Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2015 Nov 1;135:150-7. doi: 10.1016/j.colsurfb.2015.07.026. Epub 2015 Jul 21.
• Here, we have designed and synthesized a novel cationic amphiphilic stimuli-responsive azobenzene-aminoglycoside (a small molecule) conjugate, Azo-AG 5, and characterized it by UV and FTIR. Light responsive nature of Azo-AG 5 was assessed under UV-vis light. Self- assembly of Azo-AG 5 in aqueous sol
• PMID 26255160

• Quencher group induced high specificity detection of telomerase in clear and bloody urines by AIEgens.

• Zhuang Y1, Zhang M1, Chen B2, Duan R1, Min X1, Zhang Z1, Zheng F3, Liang H3, Zhao Z2, Lou X1, Xia F1.
• Analytical chemistry.Anal Chem.2015 Sep 15;87(18):9487-93. doi: 10.1021/acs.analchem.5b02699. Epub 2015 Aug 25.
• Telomerase is a widely used tumor biomarker for early cancer diagnosis. On the basis of the combined use of aggregation-induced emission (AIE) fluorogens and quencher, a quencher group induced high specificity strategy for detection of telomerase activity from cell extracts and cancer patients' urin
• PMID 26287560

Japanese Journal

• Expression and activation of EGFR and STAT3 during the multistage carcinogenesis of intrahepatic cholangiocarcinoma induced by 3'-methyl-4 dimethylaminoazobenzene in rats

• Journal of Toxicologic Pathology 28(2), 79-87, 2015
• NAID 130005072414

• Expression and activation of EGFR and STAT3 during the multistage carcinogenesis of intrahepatic cholangiocarcinoma induced by 3′-methyl-4 dimethylaminoazobenzene in rats

• Journal of Toxicologic Pathology advpub(0), 2015
• NAID 130004842622

• 初期肝障害期における血液流動性の変化

• 昭和医学会雑誌 71(6), 602-609, 2011-12
• NAID 120005536879

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英

p-dimethylaminoazobenzene, DAB

同

p-ジメチルアミノアゾベンゼン, 4-ジメチルアミノアゾベンゼン 4-dimethylaminoazobenzene、バターイエロー butter yellow、メチルイエロー methyl yellow

関

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