Basic information
- Standard SMILES
Oc1ccc2ccccc2c1N=Nc1ccc(N=Nc2ccccc2)cc1- InChIKey
FHNINJWBTRXEBC-UHFFFAOYSA-N- Molecular formula
- C22H16N4O
- Average molar mass
- 352.4 g/mol
- Monoisotopic mass
- 352.13241113
Overview
Sudan III is 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. It has a role as a carcinogenic agent, a fluorochrome and a histological dye. It is a member of azobenzenes, a member of naphthols and a bis(azo) compound. It is functionally related to a 2-naphthol.
Names & identifiers
- Preferred name
- 1-(p-Phenylazophenylazo)-2-naphthol (Sudan III)
- IUPAC
- 1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-ol
- English name
- Solvent Red 23
- Molecular formula
- C22H16N4O
- Molecular weight
- 352.39
Names & synonyms
Show more names
Database identifiers
- CAS
1071538-45-8、85-86-9- PubChem CID
- 62331
- DTXSID
DTXSID3041742- ChEMBL
CHEMBL2001927- ChEBI
CHEBI:82535- UNII
- ND733RX3JN
- EC Number
- 201-638-4、982-497-2
- Nikkaji
- J3.890C
Properties
Computed structural properties
- XLogP
- 5.9
- Topological polar surface area
- 69.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 508
Experimental & physicochemical properties
Cosmetics
Cosmetics ingredient -> Colorant
Cosmetic colorant; Hair dyeing
Ionization Efficiency
Positive
3.66
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 199 °C · 199 °C (dec.)(lit.)
- Boiling point
- 486.01 °C · 486.01°C (rough estimate)
- Density
- 1.2266 · 1.2266 (rough estimate)
- refractive index
- 1.662 · 1.6620 (estimate)
- storage temp.
- 5 °C · Store at +5°C to +30°C.
- solubility
- Insoluble in water; soluble in benzene, chloroform; moderately soluble in acetone, ether, petroleum ether; slightly soluble in ethanol, xylene
- pka
- 13.45 · 13.45±0.50(Predicted)
- form
- Powder
- Colour Index
- 26100 · 26100
- color
- Red-brown
- λmax
- 507 nm, · 507 nm, 354 nm
- Merck
- 14 · 14,8884
- BRN
- 2016384 · 2016384
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Biological Applications
- Antiseptic; preventing prostate cancer; medical devices; dental impression materials
- Major Application
- cleaning productscosmeticsfood and beveragespersonal care
- Cosmetics Ingredients Functions
- COLORANTHAIR DYEING
- InChI
- 1S/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23+,26-25+
- InChIKey
- FHNINJWBTRXEBC-HXEHWPEMSA-N
- SMILES
- Oc1ccc2ccccc2c1\N=N\c3ccc(cc3)\N=N\c4ccccc4
- LogP
- 5.74 · 5.740 (est)
- FDA 21 CFR
- 74.1317 · 74.1317; 74.2317; 74.3230;82.1317
- CAS DataBase Reference
- 85 · 85-86-9(CAS DataBase Reference)
- EWG's Food Scores
- 2 · 2-5
- FDA UNII
- 733 RX3JN · ND733RX3JN
- IARC
- 3 · 3 (Vol. 8, Sup 7) 1987
- EPA Substance Registry System
- 23 · C.I. Solvent Red 23 (85-86-9)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 317 · H317-H315-H319-H335-H341
- Precautionary statements
- 201 · P201-P305+P351+P338-P405-P501a-P261-P272-P280-P302+P352+P333+P313+P363-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 10 · 10-20-36/38-36/37/38
- Safety Statements
- 22 · 22-24/25-36-26
- WGK Germany
- 3 · 3
- RTECS
- 4250000 · QK4250000
- TSCA
- TSCA listed
- HS Code
- 32129000 · 32129000
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 20 mmol/L/5H-C · cyt-ham:ovr 20 mmol/L/5H-C ENMUDM 1,27,79
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 77.8% (175 of 225) of all reports.
Danger
H315 (21.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 225 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: 2-Naphthalenol, 1-[[4-(phenylazo)phenyl]azo]-
Hazard Traits - Bioaccumulation; Environmental Persistence
Regulation (EC) No 178/2002 (amended)
2-Naphthalenol, 1-[[4-(phenylazo)phenyl]azo]-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Skin Irrit. 2 (21.3%)
Skin Irrit. 2 (100%)
Carcinogenicity - category 2
Toxicology
Carcinogen Classification
Sudan III
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 8: (1975) Some Aromatic Azo Compounds
1987
1987
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QK4250000
- hs_code
- 32129000
- Toxicity
- cyt-ham:ovr 20 mmol/L/5H-C ENMUDM 1,27,79
- risk_code
- 10-20-36/38-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H315-H319-H335-H341
- Precautionary statements
- P201-P305+P351+P338-P405-P501a-P261-P272-P280-P302+P352+P333+P313+P363-P501
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as a biological stain; [Merck Index]
Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. The concentration limit (by weight) is 0.1%.
Household Products
Cosmetics product ingredient: 2-Naphthalenol, 1-[4-(phenylazo)phenyl]azo- (Red 17; Solvent Red 23; CI 26100; Aka225)
Information on 3 consumer products that contain D&C Red #17 in the following categories is provided:
Use Classification
Fragrance Ingredients
Cosmetics -> Cosmetic colorant; Hair dyeing
Applications
DescriptionSolvent Red 23 is an oil-soluble red azo dye used in cosmetic products in Japan. Cases were reported in hairdressers, who also reacted to PPD and to paminoazobenzene. One case of contact dermatitis was reported in the metal industry.
UsesWeakly acidic azo dye. Biological stain. Dyes and metabolites, Environmental Testing.
Preparation methods
Preparation4-(Phenyldiazenyl)benzenamine diazotization, and Naphthalen-2-ol coupling. Note: some goods by 4-(Phenyldiazenyl)benzenamine and 2-Methyl-4-(o-tolyldiazenyl)benzenamine mixture as diazo components and have to.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: 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 l pids in paraffin sections.
Related reactions
No reaction records under the current filter.
Linked notes
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