Sudan III

Names
Preferred IUPAC name

1-{[4-(Phenyldiazenyl)phenyl]diazenyl}naphthalen-2-ol

Other names

Sudan Red BK, Fat Ponceau G, Cerasin Red, C.I. 26100, Solvent Red 23, Solvent Red 164, Sudan Red, Sudan Red III, Sudan V, Sudan Red B, Sudan G, Scarlet B, and Tony Red

Identifiers

CAS Number

* 85-86-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:82535 Y

ChEMBL |

* ChEMBL2001927

ChemSpider |

* 16736189 Y

KEGG |

* C19527 Y

PubChem CID

* 62331

UNII |

* ND733RX3JN Y

InChI

* 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+ Y

Key: FHNINJWBTRXEBC-HXEHWPEMSA-N Y

* InChI=1/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+

Key: FHNINJWBTRXEBC-HXEHWPEMBU

SMILES

* Oc4ccc1ccccc1c4/N=N/c3ccc(\N=N/c2ccccc2)cc3

Properties

Chemical formula

| C22H16N4O
Molar mass | 352.397 g·mol−1
Melting point |  199 °C (390 °F; 472 K)
Hazards[1]
Safety data sheet | Sigma-Aldrich Sudan III
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H318, H319, H335, H413

GHS precautionary statements

| P101, P102, P103, P270, P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P310, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Sudan III is a lysochrome (fat-soluble dye) diazo dye. It is structurally related to azobenzene.[2]

## Contents

* 1 Uses
* 1.1 Biological staining
* 2 Safety
* 3 References
* 4 External links

## Uses

It is used to color nonpolar substances such as oils, fats, waxes, greases, various hydrocarbon products, and acrylic emulsions. Its main use is as a fuel dye in the United States of America mandated by the Internal Revenue Service (IRS) to distinguish low-taxed heating oil from automotive diesel fuel, and by the United States Environmental Protection Agency (EPA) to mark fuels with higher sulfur content; it is a replacement for Solvent Red 26 with better solubility in hydrocarbons.[3] The IRS requires "a concentration spectrally equivalent to at least 3.9 pounds of... Solvent Red 26 per thousand barrels of fuel" (11.1 mg/L);[4] the concentrations required by EPA are roughly 5 times lower. It should be stored at room temperature.[5]

### Biological staining

Sudan III is a dye used for Sudan staining. Similar dyes include Oil Red O, Sudan IV, and Sudan Black B. They are used for staining of triglycerides in frozen sections, and some protein bound lipids and lipoproteins on paraffin sections. It has the appearance of reddish brown crystals and a maximum absorption at 507(304) nm.[6] It has a more orange shade than Oil Red O, lending to its less popular status. In botany, it is used with Light Green SF Yellowish to differentiate between suberized and cutinized plant tissue.[5]

## Safety

Sudan I, Sudan III, and Sudan IV have been classified as category 3 carcinogens by the International Agency for Research on Cancer.[7]

## References

1. ↑ "Safety Data Sheet Sudan III". https://www.fishersci.com/store/msds?partNumber=S25593&productDescription=SUDAN+III+10G&vendorId=VN00115888&countryCode=US&language=en.
2. ↑ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
3. ↑ "L2_3_9_rf". http://www.chevron.com/products/prodserv/fuels/bulletin/diesel/L2_3_9_rf.htm.
4. ↑ "Publication 510: Excise Taxes (Including Fuel Tax Credits and Refunds)". IRS.gov. February 2020. p. 9. https://www.irs.gov/pub/irs-pdf/p510.pdf. Retrieved February 10, 2021.
5. ↑ 5.0 5.1 "Sudan III". https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/225/689/s4131pis.pdf.
6. ↑ R. D. Lillie. Conn's Biological Stains. Williams & Wilkins, Baltimore, MD., U.S.A.
7. ↑ "The induction of cytochrome P450 1A1 by Sudan dyes". J. Biochem. Mol. Toxicol. 22 (2): 77–84. 2008. doi:10.1002/jbt.20220. PMID 18418879.

* Susan Budavari, Editor, (1996). The Merck Index, Ed. 12. Merck & Co., Inc., Whitehouse Station, NJ, USA
* Edward Gurr, (1971). Synthetic Dyes in Biology, Medicine and Chemistry. Academic Press, London, England.

## External links

* Stains File entry

* v
* t
* e

Microbial and histological stains

Iron/hemosiderin|

* Perls' Prussian blue

Lipids|

* Sudan stain
* Sudan II
* Sudan III
* Sudan IV
* Oil Red O
* Sudan Black B

Carbohydrates|

* Periodic acid–Schiff stain

Amyloid|

* Congo red

Bacteria|

* Gram stain
* Methyl violet/Gentian violet
* Safranin
* Ziehl–Neelsen stain/acid-fast
* Carbol fuchsin/Fuchsine
* Methylene blue
* Auramine–rhodamine stain
* Auramine O
* Rhodamine B

Connective tissue|

* trichrome stain: Masson's trichrome stain/Lillie's trichrome
* Light Green SF yellowish
* Biebrich scarlet
* Phosphomolybdic acid
* Fast Green FCF

* Van Gieson's stain

Other|

* Alcian blue stain
* Cyanine
* Jaswant Singh–Bhattacharji (JSB) stain
* H&E stain
* Haematoxylin
* Eosin Y
* Janus Green B
* Giemsa stain
* Gömöri trichrome stain
* Luxol fast blue stain
* Methyl blue
* Movat's stain
* Neutral red
* Silver stain
* Bielschowsky stain
* Grocott's methenamine silver stain
* Warthin–Starry stain
* Wright's stain

Tissue stainability|

* Acidophilic
* Basophilic
* Chromophobic

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Sudan III. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Sudan_III&oldid=2862275"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H318]: Causes serious eye damage
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[H413]: May cause long lasting harmful effects to aquatic life
*[P101]: If medical advice is needed, have product container or label at hand
*[P102]: Keep out of reach of children
*[P103]: Read label before use
*[P270]: Do not eat, drink or smoke when using this product
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template