Basic information
- Standard SMILES
O=S1(=O)OC(c2ccc(O)cc2)(c2ccc(O)cc2)c2ccccc21- InChIKey
BELBBZDIHDAJOR-UHFFFAOYSA-N- Molecular formula
- C19H14O5S
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.05619455
Overview
Phenol red is 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney. It has a role as a diagnostic agent, an acid-base indicator and a two-colour indicator. It is a member of phenols, a 2,1-benzoxathiole, a sultone and an arenesulfonate ester.
Names & identifiers
- Preferred name
- Phenol Red
- IUPAC
- 4-[3-(4-hydroxyphenyl)-1,1-dioxo-2,1λ6-benzoxathiol-3-yl]phenol
- English name
- Phenol Red
- Molecular formula
- C19H14O5S
- Molecular weight
- 354.38
Names & synonyms
PHENOL REDphenolsulfonphthalein143-74-8FenolipunaSulphonthalPSP (indicator)PhenolsulphonphthaleinDTXSID8022408NSC-10459I6G9Y0J1OJDTXCID202408CHEBI:31991
Show more names
PRA-HYDROXY-A A-BIS(P-HYDROXYPHENYL)-O-TOLUENESULFONIC ACID G-SULTONEPRGRNR3C3P3532-5GPhenolrdePhenol re
Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis-, (S,S-dioxide)3,3-bis(4-hydroxyphenyl)-3H-2,1??-benzoxathiole-1,1-dioneRefChem:1728812-(Bis(4-hydroxyphenyl)methyliumyl)benzenesulfonate205-609-7SulfonphthalSulphentalPhenolred
Database identifiers
- CAS
143-74-8- PubChem CID
- 4766
- DTXSID
DTXSID8022408- ChEMBL
CHEMBL258921- ChEBI
CHEBI:31991- UNII
- I6G9Y0J1OJ
- EC Number
- 205-609-7
- Nikkaji
- J3.779.134B
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 92.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 545
Experimental & physicochemical properties
Chemical ClassesDyes -> Indicator Dyes
LogP3.02
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionOdorless, red solid; Available as pure compound, soluble monosodium salt, and dilute solutions; [CHEMINFO]
Collision Cross Section179.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2044420]
Physicochemical properties
- Melting point
- 300 °C · >300 °C
- Boiling point
- 300 °C · >300°C
- bulk density
- 200 · 200-300kg/m3
- Density
- 1.445 Mg · 1.445 Mg m-3
- refractive index
- 1.53 · 1.5300 (estimate)
- Flash point
- 300 °C · >300°C
- storage temp.
- no restrictions.
- solubility
- 1 M · 1 M NaOH: soluble1mg/mL
- form
- Solid
- pka
- 7.9 · 7.9(at 25℃)
- color
- Red
- PH Range
- 6.6 · 6.6(YELLOW)-8.0(RED)
- Odor
- Odorless
- PH
- 6.8 · 6.8~8.4
- Water Solubility
- 0.77 g/L · 0.77 g/L
- λmax
- 557 nm, · 557nm, 558nm, 360nm, 423nm, 433nm
- ε(extinction coefficient)
- 10000 at · ≥10000 at 288-294nm in H2O≥55000 at 555-561nm in H2O≥7000 at 357-363nm in H2O
- Merck
- 14 · 14,7247
- BRN
- 326470 · 326470
- Major Application
- Display device, sol-gel matrix, photoreceptors, fuel cells, waveguides, paints, detergents, cosmetics, antiperspirant composition, diapers, screening bacteria, detecting viable cells, diagnosis of urogenital ureaplasmosis, treatment of pathogen infections, amyloid-associated diseases, glaucoma, pulmonary hypertension, asthma, chronic obstructive pulmonary disease, erectile dysfunction, Raynaud’s syndrome, heparin overdose, vulvodynia, wound healing, psychoactive drugs, evaluating dental caries activity
- Cosmetics Ingredients Functions
- BUFFERING
- InChI
- 1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H
- InChIKey
- BELBBZDIHDAJOR-UHFFFAOYSA-N
- LogP
- 3.02 · 3.020
- CAS DataBase Reference
- 143 · 143-74-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- PR
- FDA UNII
- 6 G9Y0J1OJ · I6G9Y0J1OJ
- EPA Substance Registry System
- Phenol Red (143-74-8)
- UNSPSC Code
- 12352207 · 12352207
- NACRES
- 75 · NA.75
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P304+P340+P312
- target organs
- Respiratory system
- Hazard Codes
- Xi,C
- Risk Statements
- 36 · 36/37/38-34
- Safety Statements
- 37 · 37/39-26-45-36/37/39-27
- WGK Germany
- 3 · 3
- RTECS
- 7490000 · SJ7490000
- TSCA
- TSCA listed
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 STOT · Skin Irrit. 2STOT SE 3
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >600 mg/kg CTOXAO 4(2),185,71
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.4% (3 of 211) of reports.
Warning
H315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 211 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis-, S,S-dioxide
Phenolsulfonphthalein: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryDust may be irritating if inhaled; [CHEMINFO]
Hazard Classes and CategoriesSkin Irrit. 2 (98.6%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SJ7490000
- hs_code
- 29349990
- Toxicity
- LD50 orl-rat: >600 mg/kg CTOXAO 4(2),185,71
- risk_code
- 36/37/38-34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C
- safety_code
- 37/39-26-45-36/37/39-27
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H335
- Hazard Classifications
- Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P304+P340+P312
Chemistry & industry
Pharmacology
ATC Code
V - Various
QV - Various
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
Uses & manufacturing
UsesUsed as a pH indicator and marker of kidney function and other physiological functions; [CHEMINFO] Used as a pH indicator for the pH range of 6.4-8.2; [Ullmann]
Household ProductsInformation on 1 consumer products that contain Phenolsulfonphthalein in the following categories is provided:
General Manufacturing InformationPhenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis-: ACTIVE
Applications
DescriptionPhenol red belongs to the class of triphenylmethane dyes and is widely used in the textile industry.
UsesAs indicator in 0.02-0.05% alcohol solution. pH 6.8 yellow, 8.4 red.
UsesPhenol red is used as a non absorbed marker in gravimetric method. It is a pH indicator used in cell biology laboratories and in home swimming pool test kits. It is used to check the kidney function based on the excreted phenol red by colorimetric method.
UsesPhenol red solution acts as a pH indicator for the culture medium.
Preparation methods
PreparationPhenol red is prepared in Dulbecco′s Phosphate Buffered Saline.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
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Additional notes
DefinitionChEBI: 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.
Related reactions
6 records
Linked notes
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