1-[(E)-2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl]naphthalen-2-ol

• ChemBase ID: 103538
• Molecular Formular: C22H16N4O
• Molecular Mass: 352.38864
• Monoisotopic Mass: 352.13241115
• SMILES: Oc1ccc2ccccc2c1/N=N/c1ccc(cc1)/N=N/c1ccccc1
• Canonical SMILES: Oc1ccc2c(c1/N=N/c1ccc(cc1)/N=N/c1ccccc1)cccc2
• 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
• InChIKey: FHNINJWBTRXEBC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(E)-2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl]naphthalen-2-ol; 1-{2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl}naphthalen-2-ol; 1-[(E)-2-{4-[(E)-2-phenyldiazen-1-yl]phenyl}diazen-1-yl]naphthalen-2-ol
• IUPAC Traditional name: 1-[(E)-2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl]naphthalen-2-ol; 1-{2-[4-(2-phenyldiazen-1-yl)phenyl]diazen-1-yl}naphthalen-2-ol; oil red
• Synonyms: C.I. 26100; SUDAN III; 1-[4-(Phenylazo)phenylazo]-2-naphthol; Cerasin Red; Fat Ponceau G; Fat Soluble Sudan; Scarlet B; Solvent Red 23; Sudan G; Sudan Red BK; Tony Red; Sudan III; 1-[2-[4-(2-Phenyldiazenyl)phenyl]diazenyl]-2-naphthalenol; 1-[[4-(Phenylazo)phenyl]azo]-2-naphthalenol; Sudan 3; 1-(p-Phenylazophenylazo)-2-naphthol; 111440 Red; Toney Red; 苏丹红III; 1-[(4-苯基偶氮)苯基]偶氮-2-萘酚; 樱胶素红; 溶剂红 23; 猩红 B; 脂溶性苏丹; 脂肪丽春红 G; 苏丹红 BK; 苏丹红 G; 黄光油溶红; 苏丹 III

Database IDs

• CAS Number: 85-86-9
• EC Number: 201-638-4
• MDL Number: MFCD00003905
• Beilstein Number: 931185
• Merck Index: 148884
• PubChem SID: 162090423; 24899589; 24899586
• PubChem CID: 5379348
• Chemspider ID: 16736189
• KEGG ID: C19527
• Unique Ingredient Identifier: ND733RX3JN
• Wikipedia Title: Sudan_III
• Color Index Number: 26100

CALCULATED PROPERTIES

• Acid pKa: 11.335522
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 7.4709415
• LogD (pH = 7.4): 7.4708943
• Log P: 7.4709444
• Molar Refractivity: 113.1271 cm^3
• Polarizability: 40.959557 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Red Solid
• Melting Point: 197-199°C; 199 °C; 199 °C (dec.)(lit.); 199°C; ca 200°C dec.

Safety Information

• Storage Condition: Amber Vial, Refrigerator; Room Temperature (15-30°C)
• RTECS: QK4250000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-68
• Safety Statements: 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Hazard statements: H341-H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥96.0% (HPLC); Dye Content ~75%
• Grade: analytical standard, for food analysis; certified by the Biological Stain Commission; for microscopy
• Compostion: Dye content, ≥80%
• Empirical Formula (Hill Notation): C22H16N4O

DETAILS

MP Biomedicals - 02152087

C.I. 26100
Dye Content: ~ 75%

MP Biomedicals - 05218907

MP Biomedicals Rare Chemical collection

Sigma Aldrich - S4136

Suitability
Certified as a fat staining using the Churukian variant of the Lillie-Ashburn supersaturated isopropanol method. Sudan III is substituted for the oil red O in the procedure.

Toronto Research Chemicals - S688900

Weakly acidic azo dye. Biological stain.

REFERENCES

• Stiborova, M., et al.: Cancer Res., 62, 5678 (2002)
• Chen, H., et al.: Microbiology, 151, 1433 (2002)
• An, Y., et al.: Mutat. Res., 627, 164 (2002)
• Wang, S., et al.: J. Agric. Food Chem., 55, 3869 (2002)