Page last updated: 2024-11-06

sudan iii

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Description

Sudan III is a bright red diazo dye that is insoluble in water but soluble in fats and oils. It is synthesized by coupling 1-naphthylamine with diazotized 2,4-dinitrochlorobenzene. Sudan III is used as a stain for lipids and fats, and it is also used as an indicator for the presence of unsaturated fatty acids. In biological research, Sudan III is used to stain lipid droplets in cells and tissues, and it is also used to assess the lipid content of food products. Sudan III has been reported to have carcinogenic properties, and it is therefore no longer widely used as a food additive. However, it is still used in some research settings.'

sudan III: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Sudan III : A bis(azo) compound that is 2-naphthol substituted at position 1 by a 4-{[(2-methylphenyl)diazenyl]phenyl}diazenyl group. A fat-soluble dye predominantly used for demonstrating triglycerides in frozen sections, but which may also stain some protein bound lipids in paraffin sections. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID62331
CHEMBL ID2001927
CHEBI ID82535
SCHEMBL ID52298
SCHEMBL ID331733
SCHEMBL ID11882848
SCHEMBL ID11882853
SCHEMBL ID10294618
SCHEMBL ID506289
SCHEMBL ID20138219
MeSH IDM0102605

Synonyms (151)

Synonym
nsc65825
nsc-65825
LS-14923
c.i. solvent red 23
red zh
d and c red no. 17
2-naphthalenol, 1-[[4-(phenylazo)phenyl]azo]-
fettrot
pyronalrot b
motirot 2r
somalia red iii
fat red r
wln: l66j bnunr dnunr&& cq
solvent red 23
cerotinscharlach r
soudan iii
sudan g iii
sudan p iii
rot g
fat red, bluish
schultz no. 31
sudan iii, g
fat soluble red zh
grasal brilliant red g
fat scarlet lb
fettscharlach lb
toney red
stearix scarlet
sudan iii
benzeneazobenzeneazo-.beta.-naphthol
1-[[4-(phenylazo)phenyl]azo]-2-naphthalenol
silotras scarlet tb
c.i. 23
c.i. 26100
nsc-8995
rouge cerasine
tetrazobenzene-.beta.-naphthol
fat red hrr
fettscharlach
cerasinrot
1-(phenylazophenylazo)-2-hydroxynaphthalene
111440 red
organol scarlet
sudan red iii
tony red
ponceau, olg
2-naphthol, 1-[[p-(phenylazo)phenyl]azo]-
1-[[p-(phenylazo)phenyl]azo]-2-naphthol
85-86-9
fd and c red no. 17
cerasin red
organol red bs
rot c
grasan brilliant red g
fettponceau g
red no. 225
d & c red no. 17
nsc8995
brn 0931185
sudan 3
fat red (bluish)
2-naphthol, 1-((p-(phenylazo)phenyl)azo)-
1-((p-phenylazo)phenyl)azo-2-naphthol
einecs 201-638-4
cerven rozpoustedlova 23 [czech]
japan red 225
1-(4-(phenylazo)phenylazo)-2-naphthol
ccris 7074
nsc 65825
fat red, bluish (van)
2-naphthalenol, 1-((4-(phenylazo)phenyl)azo)-
sudan iii (g)
benzeneazobenzeneazo-beta-naphthol
ai3-02854
1-((4-(phenylazo)phenyl)azo)-2-naphthalenol
ci 26100
ponceau, insoluble, olg
fat red rs
tetrazobenzene-beta-naphthol
sudan iii, technical grade
sudan iii, certified by the biological stain commission, bioxtra
d & c red #17
S0142
AKOS003581971
C19527
STL256855
1-[(e)-{4-[(e)-phenyldiazenyl]phenyl}diazenyl]naphthalen-2-ol
1-{[4-(phenyldiazenyl)phenyl]diazenyl}naphthalen-2-ol
cerven rozpoustedlova 23
2-naphthalenol, 1-(2-(4-(2-phenyldiazenyl)phenyl)diazenyl)-
nd733rx3jn ,
unii-nd733rx3jn
4-16-00-00248 (beilstein handbook reference)
FT-0631403
dc red no. 17
sudan iii [iarc]
red 17
red 17 [inci]
d & c red #17 [vandf]
d&c red dye no 17
d&c red no.17
aka225
d & c red no.17 k7007
solvent red 23 [inci]
a204 tudor phlox
ci 26100 [inci]
2-naphthol, 1-(p-phenyulazophenylazo)-
aka225 [inci]
sudan iii [mi]
d&c red no. 17
sudan red bk
1-{2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl}naphthalen-2-ol
1-[4-(phenylazo)phenylazo]-2-naphthol
S5165
SCHEMBL52298
SCHEMBL331733
CHEBI:82535
SCHEMBL11882848
SCHEMBL11882853
SCHEMBL10294618
SCHEMBL506289
CHEMBL2001927
dc red 17
2-naphthalenol, 1-[2-[4-(2-phenyldiazenyl)phenyl]diazenyl]-
1-((4-[phenyldiazenyl]phenyl)diazenyl)-2-naphthol
DTXSID3041742
mfcd00003905
AKOS028109139
sudan iii, analytical standard
sudan red (chromatographic standard)
1-((e)-(4-((e)-phenyldiazenyl)phenyl)diazenyl)-naphthalen-2-ol
sudanrot
1071538-45-8
HY-D0931
E75949
sudan iiisolvent red 23
1-[(e)-[4-[(e)-phenylazo]phenyl]azo]naphthalen-2-ol
Q1187765
1-((e)-{4-[(e)-phenyldiazenyl]phenyl}diazenyl)-2-naphthol
SCHEMBL20138219
1-((e)-(4-((e)-phenyldiazenyl)phenyl)diazenyl)naphthalen-2-ol
EN300-631706
CS-0016887
1-((4-(phenyldiazenyl)phenyl)diazenyl)naphthalen-2-ol
CCG-268054
sudan 3 100 microg/ml in acetonitrile
1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-ol
sudan ?
sudan red iii, sudan iii, c.i. 26100
CS-0168962
1-((4-(phenyldiazenyl)phenyl)diazenyl)naphthalen-2-ol, tech grade

Research Excerpts

Overview

Sudan III is a coloring agent used in chemical industries and food additives.

ExcerptReferenceRelevance
"Sudan III is a coloring agent used in chemical industries and food additives. "( Investigation on the interaction of food colorant Sudan III with bovine serum albumin using spectroscopic and molecular docking methods.
Bai, J; Ma, X; Sun, X, 2020
)
2.25

Effects

ExcerptReferenceRelevance
"Sudan III has been shown to be carcinogenic to human beings due to the azo chemical structure. "( Separation and Enrichment of Sudan III Using Surface Modified Hollow Glass Microspheres and Colorimetric Detection.
Chen, F; Wu, S; Yu, Y; Zhang, C, 2021
)
2.36

Treatment

Sudan III (S.III) treatment induced CYP 1A1 and CYC 1A2 protein expression, mRNA and their metabolic activities. Treatment of Long-Evans rats results in increased hepatic monooxygenase activity using ethoxycoumarin and aniline as substrates.

ExcerptReferenceRelevance
"Sudan III (S.III) treatment induced CYP 1A1 and CYP 1A2 protein expression, mRNA and their metabolic activities, methoxyresorufin-O-demethylase (MROD) and ethoxyresorufin-O-deethylase (EROD), in Wistar rats higher than those in the control."( PPARalpha-dependent modulation of hepatic CYP1A by clofibric acid in rats.
El-Shazly, S; Fujita, S; Ishizuka, M; Kazusaka, A; Kimura, K; Shaban, Z, 2004
)
1.04
"Sudan III pretreatment increased extensively PL 4-hydroxylase, 5-hydroxylase and N-desisopropylase activities at high but not at low PL concentrations."( Induction of propranolol metabolism by the azo dye sudan III in rats.
Fujita, S; Ishida, R; Masubuchi, Y; Narimatsu, S; Obara, S; Suzuki, T, 1992
)
1.26
"Sudan III treatment of Long-Evans rats results in increased hepatic monooxygenase activity using ethoxycoumarin and aniline as substrates. "( Alterations in the metabolism of 7,12-dimethylbenz[a]anthracene and various xenobiotics by rat hepatic microsomes following Sudan III treatment in vivo.
Bulleid, NJ; Burnett, AK; Craft, JA; O'Dowd, JJ; Weston, A, 1985
)
1.92

Compound-Compound Interactions

ExcerptReferenceRelevance
"A simple and highly selective molecularly imprinted solid-phase extraction (MISPE) combined with ultrasound-assisted dispersive liquid-liquid microextraction (DLLME) was developed for the determination of four Sudan dye (I, II, III, and IV) residues in sausage products."( Molecularly imprinted solid-phase extraction combined with ultrasound-assisted dispersive liquid-liquid microextraction for the determination of four Sudan dyes in sausage samples.
Qiao, J; Row, KH; Wang, H; Yan, H; Yang, G, 2011
)
0.37
"A method for the simultaneous determination of Sudan I, II, III, and IV in blood samples by solid-phase extraction (SPE) combined with ultra-fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS) has been established."( [Simultaneous determination of four Sudan dyes in blood by solid-phase extraction combined with ultra-fast liquid chromatography-tandem mass spectrometry].
Chen, X; Fu, J; Hu, Y; Huang, K; Huang, X; Jin, M; Zhu, H; Zou, B, 2014
)
0.4

Dosage Studied

ExcerptRelevanceReference
" Animals dosed for 7 days with 13cisRA, retinyl acetate, or 4HPR showed a 38, 27, and 40% reduction in binding of benzo(a)pyrene to liver DNA and a 29, 32, and 21% reduction in binding to stomach DNA, respectively, when the carcinogen was administered on the eighth day, and the tissues were harvested 24 h later."( Effects of retinoids on metabolizing enzymes and on binding of benzo(a)pyrene to rat tissue DNA.
Hill, DL; Lindamood, C; McCarthy, DJ, 1987
)
0.27
"Methods of isotonic regression are proposed to increase the power of common trend tests in situations where a monotonicity constraint is imposed upon the dose-response function."( Order-restricted dose-related trend tests.
Ahn, H; Chen, JJ; Mancuso, JY, 2001
)
0.31
"A simple, rapid, accurate sensitive spectrophotometry procedure for the determination of amoxycillin (Amox) and flucloxacillin (Fluclox) in bulk samples and in dosage forms are developed."( Utilization of ion exchanger and spectrophotometry for assaying amoxycillin and flucloxacillin in dosage form.
Aly, HM; Amin, AS, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
fluorochromeA fluorescent dye used to stain biological specimens.
histological dyeA dye used in microscopic or electron microscopic examination of cells and tissues to give contrast and to highlight particular features of interest, such as nuclei and cytoplasm.
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
azobenzenesAny member of the wide class of molecules that share the core azobenzene structure, comprising two phenyl rings linked by a N=N double bond, which may have different functional groups extending from the rings.
bis(azo) compoundAny azo compound containing two -N=N- groups.
naphtholsAny hydroxynaphthalene derivative that has a single hydroxy substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (145)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (19.31)18.7374
1990's11 (7.59)18.2507
2000's40 (27.59)29.6817
2010's51 (35.17)24.3611
2020's15 (10.34)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 74.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index74.37 (24.57)
Research Supply Index5.04 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index125.97 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (74.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.66%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (1.32%)4.05%
Observational0 (0.00%)0.25%
Other149 (98.03%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]