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Metanil yellow

PubChem CID
3935589
Structure
Metanil yellow_small.png
Metanil yellow_3D_Structure.png
Molecular Formula
Synonyms
  • Metanil yellow
  • ACID YELLOW 36
  • 587-98-4
  • C.I. Acid Yellow 36
  • Acid Metanil Yellow
Molecular Weight
375.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-09-12
  • Modify:
    2025-01-18
Description
Metanil yellow is an organic sodium salt having 3-[(4-anilinophenyl)diazenyl]benzene-1-sulfonate as the counterion. Used in one variant of Masson's trichrome to stain collagen yellow in contrast to the red muscle, but is not in common used. It has a role as a histological dye. It contains a 3-[(4-anilinophenyl)diazenyl]benzene-1-sulfonate.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Metanil yellow.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H15N3O3S.Na/c22-25(23,24)18-8-4-7-17(13-18)21-20-16-11-9-15(10-12-16)19-14-5-2-1-3-6-14;/h1-13,19H,(H,22,23,24);/q;+1/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NYGZLYXAPMMJTE-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C(C=C1)NC2=CC=C(C=C2)N=NC3=CC(=CC=C3)S(=O)(=O)[O-].[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H14N3NaO3S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

587-98-4
1173501-41-1
53988-78-6
68417-63-0
84842-92-2

2.3.3 Deprecated CAS

1173501-41-1, 53988-78-6, 68417-63-0, 84842-92-2
53988-78-6, 84842-92-2

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 DSSTox Substance ID

2.3.8 NCI Thesaurus Code

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • acid yellow 36
  • metanil yellow
  • metanil yellow, monosodium salt
  • sodium 3-((4-anilinophenyl)azo)benzenesulfonate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
375.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
375.06535677 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
375.06535677 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
102 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
538
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Other Solid
Brownish-yellow solid; [Merck Index] Powder; [Sigma-Aldrich MSDS]

3.2.2 Dissociation Constants

3.3 Chemical Classes

Dyes -> Azo Dyes

5 Chemical Vendors

6 Food Additives and Ingredients

6.1 Color Additive Status

Color Additive
Use
None
Former Use
formerly External Drugs, External Cosmetics
Color additive regulations in 21 eCFR

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Adjuvants, Immunologic
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)
Coloring Agents
Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)
Food Coloring Agents
Natural or synthetic dyes used as coloring agents in processed foods. (See all compounds classified as Food Coloring Agents.)

8 Use and Manufacturing

8.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as an indicator; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA] Used in leather dyeing; [PMID 21938525]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Industrial Processes with risk of exposure
Leather Tanning and Processing [Category: Industry]

8.1.1 Consumer Uses

Pigment

8.1.2 Household Products

Household & Commercial/Institutional Products

Information on 9 consumer products that contain C.I. Acid Yellow in the following categories is provided:

• Auto Products

• Commercial / Institutional

• Inside the Home

8.2 U.S. Production

Aggregated Product Volume
2019: 27,200 lb

8.3 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzenesulfonic acid, 3-[2-[4-(phenylamino)phenyl]diazenyl]-, sodium salt (1:1): ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 5
View All
Note
Pictograms displayed are for 82% (356 of 434) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 18% (78 of 434) of reports.
Pictogram(s)
Corrosive
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H302 (11.8%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (12.4%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H317 (44.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (25.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (11.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (12.4%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H361f (20%): Suspected of damaging fertility [Warning Reproductive toxicity]

H411 (38.5%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

H412 (11.5%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 434 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 78 of 434 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 20 notifications provided by 356 of 434 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (11.8%)

Acute Tox. 4 (12.4%)

Skin Sens. 1 (44.7%)

Eye Dam. 1 (25.8%)

Eye Irrit. 2 (11.5%)

Acute Tox. 4 (12.4%)

Repr. 2 (20%)

Aquatic Chronic 2 (38.5%)

Aquatic Chronic 3 (11.5%)

Eye Irrit. 2 (100%)

9.1.3 Hazards Summary

Causes normocytic anemia in 26-week constant oral studies of mice; Causes degenerative changes to brain, liver changes, and effects on other transferases in repeated-dose oral studies of rats; [RTECS] A skin sensitizer; [PMID 21938525] May cause irritation and skin sensitization; [Sigma-Aldrich MSDS]

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzenesulfonic acid, 3-[[4-(phenylamino)phenyl]azo]-, monosodium salt
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Benzenesulphonic acid, 3-[[4-(phenylamino)phenyl]azo]-, monosodium salt: Does not have an individual approval but may be used under an appropriate group standard

9.3 Other Safety Information

Chemical Assessment
IMAP assessments - Miscellaneous azodyes: Human health tier II assessment

10 Toxicity

10.1 Toxicological Information

10.1.1 Adverse Effects

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

10.1.2 Acute Effects

11 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 ChemIDplus

15.5 UN GHS Classification

15.6 EPA CPDat Classification

15.7 NORMAN Suspect List Exchange Classification

15.8 EPA DSSTox Classification

15.9 Consumer Product Information Database Classification

15.10 EPA TSCA and CDR Classification

15.11 EPA Substance Registry Services Tree

15.12 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Benzenesulfonic acid, 3-[[4-(phenylamino)phenyl]azo]-, monosodium salt
    https://services.industrialchemicals.gov.au/search-assessments/
    Benzenesulfonic acid, 3-[[4-(phenylamino)phenyl]azo]-, monosodium salt
    https://services.industrialchemicals.gov.au/search-inventory/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
    Benzenesulfonic acid, 3-[2-[4-(phenylamino)phenyl]diazenyl]-, sodium salt (1:1)
    https://www.epa.gov/chemical-data-reporting
  4. EPA Chemicals under the TSCA
    Benzenesulfonic acid, 3-[2-[4-(phenylamino)phenyl]diazenyl]-, sodium salt (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    C.I. Acid Yellow 36, monosodium salt
    https://comptox.epa.gov/dashboard/DTXSID5041722
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Sodium 3-(p-anilinophenylazo)benzenesulphonate
    https://chem.echa.europa.eu/100.008.736
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.281.418
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.281.421
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.281.425
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.281.426
    Sodium 3-(p-anilinophenylazo)benzenesulphonate (EC: 209-608-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/21193
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate (EC: 844-658-4)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/290194
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate (EC: 844-662-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/290197
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate (EC: 844-666-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/290201
    sodium;3-[(4-anilinophenyl)diazenyl]benzenesulfonate (EC: 844-667-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/290202
  7. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  9. ChEBI
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  12. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  13. EPA Chemical and Products Database (CPDat)
  14. FDA Regulatory Status of Color Additives
  15. IUPAC Digitized pKa Dataset
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  18. Springer Nature
  19. Wikidata
  20. Wikipedia
  21. PubChem
  22. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  23. GHS Classification (UNECE)
  24. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  25. EPA Substance Registry Services
  26. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  27. PATENTSCOPE (WIPO)
CONTENTS