CAS 548-62-9|CAS 14426-25-6|CAS 39393-39-0|CAS 8004-87-3|4-{bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium chloride|CARBOL CRYSTAL VIOLET|gentian violet chloride|结...

General Information

Structure

Molecular Formula

C₂₅H₃₀ClN₃

Molecular Mass

407.9788

Exact Mass

407.21282566

Charge

InChI

InChI=1S/C25H30N3.ClH/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6;/h7-18H,1-6H3;1H/q+1;/p-1

InChIKey

ZXJXZNDDNMQXFV-UHFFFAOYSA-M

Canonic Smiles

C[N+](=C1C=CC(=C(c2ccc(cc2)N(C)C)c2ccc(cc2)N(C)C)C=C1)C.[Cl-]

Isomeric Smiles

N(c1ccc(/C(=C/2\C=CC(=[N+](C)C)C=C2)/c2ccc(N(C)C)cc2)cc1)(C)C.[Cl-]

Calculated Properties

JChem

LogD (pH = 7.4)

1.39

LogD (pH = 5.5)

1.31

Log P

1.40

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.83

Polar Surface Area

9.49

Polarizability

45.65

Molar Refractivity

146.00

Data Source

Names and Identifiers

IUPAC name

4-{bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium chloride

Synonyms

CARBOL CRYSTAL VIOLET结晶紫龙胆紫甲基紫 10B碱性紫 3六甲副蔷薇苯胺氯化物Crystal VioletCrystal violet Gentian violet龙胆紫BRILLIANT VIOLET结晶紫Gentian VioletGentian VioletMethyl Violet 10BBasic Violet 3Hexamethylpararosaniline chlorideCrystal VioletGENTIAN VIOLET, ACSMethyl violetGentian Violet BCARBOL GENTIAN VIOLETCrystal violet solution结晶紫溶液Violet XXIIIOxiuranAdergonOxyozylMeroxylGentersalN-[4-[Bis[4-(dimethylamino)phenyl]methylene]-2,5-cyclohexadien-1-ylidene]-N-methylmethanaminium ChlorideViolet CPCrystal Violet ChlorideOxycolorHEXAMETHYL VIOLETGram-Hucker’s stain solution (I)Gentian Violet solution龙胆紫溶液Gentian Violet solutionGram-Hucker’s stain solution (I)Methylrosaniline chlorideC.I. 42555Crystal Violet, ACS结晶紫, ACSCalcozine Violet CBismuth VioletGentianaviolett(4-{bis[-(dimethylamino)phenyl]methylene}-2,5-cyclohexadien-1-ylidene)dimethylammonium chloridemethylrosaniline chlorideN-(-4-{bis[4-(dimethylamino)phenyl]methylene}2,5-cyclohexadien-1-ylidene)-N-methyltrimethanaminium chloridecrystal violetBrilliant Violet 5BCI Basic Violet 3C.I. 42555hexamethylpararosaniline chlorideBasic Violet BNGentian violetCalcozine Violet 6BNBlaues pyoktaninN-(4-{bis[4-(dimethylamino)phenyl]methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminiumC.I. Basic violet 3aniline violethexamethyl-p-rosaniline chlorideCI 42555Basic Violet 3

IUPAC Traditional name

gentian violet chloride crystal violet

Brand Name

Paper Blue RHidaco Brilliant Crystal VioletMethyl Violet 10BKGentiolettenCrystal Violet 5BOMethyl Violet 10BMethyl Violet 10BOCrystal Violet Extra Pure APNXCrystal Violet OPyoktaningentian violet grmethylrosanilinium chlorideCrystal Violet USPAizen Crystal Violet Extra PureBasic Violet BNMeroxyl-WanderBadilCrystal Violet AOAniline VioletOxycolorGentiavermCrystal Violet BPCCrystal Violet baseHecto Violet RCrystal Violet Extra PureCrystal Violet 10Bgention violet alchoholic staining solutionAdergonMeroxylan-WanderCrystal Violet Extra Pure APNBismuth VioletMethyl violet

API Name

Gentian Violet

International Nonproprietary Name (INN)

chlorure de methylrosaniliniummethylrosanilinii chloridummethylrosanilinium chloridecloruro de metilrosanilina

Names and Identifiers

Registration numbers

PubChem SID

1609637522485976824859619248922722489265124895083248958952487229646505353248700822489284224882056223438474

PubChem CID

EC Number

MDL Number

Merck Index

CAS Number

548-62-914426-25-639393-39-08004-87-3

Beilstein Number

407770835809488464808

Color Index Number

42555

CHEMBL

64894CHEMBL64894

Wikipedia Title

Methyl_violetCrystal_violet

Chemspider ID

170606

DrugBank ID

DB00406

BRENDA Database

2.7.8.141.8.1.122.7.8.121.11.1.191.11.1.73.1.21.11.11.1.102.3.1.281.10.3.2

PubMed Citation Links

241182766304876236644762300786243409431509942272286210955302359811323724934184645262346579321324408228897417456163151757

KEGG DRUG Database

D01046

BKMS React Database

44145441524384246031

ACToR Database

548-62-923355-47-7

UniProt Database

P37637P33335Q8G2M6P0AFS5P37636

CHEBI ID

CHEBI:3933CHEBI:41688

BRENDA Ligand Database

43842460314414544152

PDBeChem Database

CVI

MetaboLights Database

MTBLS2737MTBLS2291MTBLS3750MTBLS2145

CompTox Database

HMDB Database

SureChEMBL Database

Reaxys Registry

Registration numbers

Properties

Safety Information

-20°C

Room Temperature (15-30°C), Protect from light

Room Temperature (15-30°C)

Amber Vial, Refrigerator

Harmful (Xn)

Properties

Related Proteins

No Data Available

Click here to submit data

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00406

Drug Groups

approved

Description

A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties. [PubChem]

Indication

For the treatment of bacterial and fungal infections inside the mouth (thrush) and skin, also for the prevention of transmission of Chagas' disease (as a blood additive).

Pharmacology

Gentian violet is a mutagen, a mitotic poison, and a clastogen. Gentian violet has been used in medicine for almost 100 years: as an antiseptic for external use, as a topical antibiotic, as a topical antifungal agent, as an antihelminthic agent by oral administration, and more recently, as a blood additive to prevent transmission of Chagas' disease. It is thought to work by binding to the DNA of target organisms and causing disruption, mutation or inhibition of DNA replication.

Toxicity

LD₅₀=420 mg/kg (rat, oral). Oral administration can cause gastrointestinal irritation, and intravenous injection can cause depression in the white blood cell count.

Affected Organisms

Yeast and other fungi

Bacteria and protozoa

Biotransformation

Primarily hepatic, mostly demethylation

External Links

• [Wikipedia]

• [Drugs.com]

Selleck Chemicals

S1917

Research Area: Infection
Biological Activity:
Crystal violet is a triarylmethane dye. The dye is used as a histological stain and in Gram’s method of classifying bacteria. Crystal violet has antibacterial, antifungal and anthelmintic properties,which was formerly important as a topical antiseptic. [1]

MP Biomedicals

02101775

Dye content: ~ 95%

02152511

ACS Reagent Grade
Assay ≥90.0% anhydrous dye

05207018

MP Biomedicals Rare Chemical collection

05207551

MP Biomedicals Rare Chemical collection

05208589

MP Biomedicals Rare Chemical collection

05213025

MP Biomedicals Rare Chemical collection

Wikipedia

Methyl_violet

Sigma Aldrich

G2039

Application
Gentian Violet is the primary stain used in the Gram stain technique for differentiation of Gram-negative versus Gram-postive bacteria. Used as a component of CV cytotoxicity assays.

C6158

包装
50, 100 g in glass bottle

C3886

Application
Crystal Violet is the primary stain used in the Gram stain technique for differentiation of Gram-negative versus Gram-postive bacteria. Used as a component of CV cytotoxicity assays.

C0775

Application
Used as the active component, primary stain, of Gram stain for differentiation of Gram-negative versus Gram-postive bacteria.
包装
25, 100 g in glass bottle
Suitability
Certified for use with the Gram stain for bacteria, Flemming triple stain with iodine for chromosomes, Lieb′s amyloid stain and Newton′s crystal violet-iodine technique for chromatin and nucleoli.

32909

General description
Visit our Titration Center to learn more.

46364

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

229288

Packaging
25, 100 g in glass bottle

12-0330

Suitability
bacterial staining

12-1521

Components
Composition : Crystal violet in water

49144

Components
Composition : Gentian violet 5.0 g/l in water
General description
Gentian violet is used in the Gram staining for distinguishing between gram-positive and gram-negative organisms.

HT901

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Components
HT901 is composed of certified crystal violet, 2.3%, ammonium oxalate, 0.1%, and 20% ethyl alcohol, SD3A.
Application
Kit component of Gram Stain kits HT90A and HT90T (for staining of heat-fixed films and tissue, respectively).

HT90132

Components
Contains 2.3% certified crystal violet, 0.1% ammonium oxalate and 20% ethyl alcohol, SD3A.
Application
Intended for use in the Gram Stain Procedure No. HT90.

48770

General description
mixture of crystal violet [C.I.No. 42555] and methyl violet [C.I.No. 42535]
Other Notes
Dye employed for preparing Gram stain1

TRC

G362500

Anti-infective (topical). Has been used as anthelmintic (Nematodes).

ChEBI

CHEBI:41688

An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Crystal_violet

• Docampo, R., et al.: Drug Metab. Rev., 22, 161 (1972)

• Hodge, H.C., et al.: Toxicol. Appl. Pharmacol., 22, 1 (1972)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule Details

DrugBank

DB00406

Drug Groups

approved

Description

A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties. [PubChem]

Indication

For the treatment of bacterial and fungal infections inside the mouth (thrush) and skin, also for the prevention of transmission of Chagas' disease (as a blood additive).

Pharmacology

Toxicity

LD₅₀=420 mg/kg (rat, oral). Oral administration can cause gastrointestinal irritation, and intravenous injection can cause depression in the white blood cell count.

Affected Organisms

Yeast and other fungi

Bacteria and protozoa

Biotransformation

Primarily hepatic, mostly demethylation

External Links

• [Wikipedia]

• [Drugs.com]

S1917

Dye content: ~ 95%

ACS Reagent Grade
Assay ≥90.0% anhydrous dye

05207018

MP Biomedicals Rare Chemical collection

05207551

MP Biomedicals Rare Chemical collection

05208589

MP Biomedicals Rare Chemical collection

05213025

MP Biomedicals Rare Chemical collection

Wikipedia

Methyl_violet

Sigma Aldrich

G2039

Application
Gentian Violet is the primary stain used in the Gram stain technique for differentiation of Gram-negative versus Gram-postive bacteria. Used as a component of CV cytotoxicity assays.

C6158

包装
50, 100 g in glass bottle

C3886

Application
Crystal Violet is the primary stain used in the Gram stain technique for differentiation of Gram-negative versus Gram-postive bacteria. Used as a component of CV cytotoxicity assays.

C0775

32909

General description
Visit our Titration Center to learn more.

46364

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

229288

Packaging
25, 100 g in glass bottle

12-0330

Suitability
bacterial staining

12-1521

Components
Composition : Crystal violet in water

49144

Components
Composition : Gentian violet 5.0 g/l in water
General description
Gentian violet is used in the Gram staining for distinguishing between gram-positive and gram-negative organisms.

HT901

HT90132

Components
Contains 2.3% certified crystal violet, 0.1% ammonium oxalate and 20% ethyl alcohol, SD3A.
Application
Intended for use in the Gram Stain Procedure No. HT90.

48770

General description
mixture of crystal violet [C.I.No. 42555] and methyl violet [C.I.No. 42535]
Other Notes
Dye employed for preparing Gram stain1

TRC

G362500

Anti-infective (topical). Has been used as anthelmintic (Nematodes).

ChEBI

CHEBI:41688

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Crystal_violet

• Docampo, R., et al.: Drug Metab. Rev., 22, 161 (1972)