Thymol blue

Last updated
Thymol blue
Thymolblau skeletal.png
Thymol Blue crystals.jpg
Names
Preferred IUPAC name
3,3-Bis[4-hydroxy-2-methyl-5-(propan-2-yl)phenyl]-2,1λ6-benzoxathiole-1,1(3H)-dione
Other names
α-hydroxy-α,α-bis(5-hydroxycarvacryl)- o-toluenesulfonic acid γ-sultone; thymolsulfonephthalein
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.886 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-973-3
PubChem CID
UNII
  • InChI=1S/C27H30O5S/c1-15(2)19-13-22(17(5)11-24(19)28)27(21-9-7-8-10-26(21)33(30,31)32-27)23-14-20(16(3)4)25(29)12-18(23)6/h7-16,28-29H,1-6H3 Yes check.svgY
    Key: PRZSXZWFJHEZBJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C27H30O5S/c1-15(2)19-13-22(17(5)11-24(19)28)27(21-9-7-8-10-26(21)33(30,31)32-27)23-14-20(16(3)4)25(29)12-18(23)6/h7-16,28-29H,1-6H3
    Key: PRZSXZWFJHEZBJ-UHFFFAOYAE
  • O=S2(=O)OC(c1ccccc12)(c3cc(c(O)cc3C)C(C)C)c4cc(c(O)cc4C)C(C)C
Properties
C27H30O5S
Molar mass 466.59 g·mol−1
AppearanceBrownish-green crystal powder
Melting point 221–224 °C (430–435 °F; 494–497 K)
decomposes [1]
Insoluble
UV-vismax)594 nm (1st)
376 nm (2nd) [1]
Hazards
Main hazards Harmful
GHS classification and labelling: [2]
GHS-pictogram-exclam.svg
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
1
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thymol blue (thymolsulfonephthalein) is a brownish-green or reddish-brown crystalline powder that is used as a pH indicator. It is insoluble in water but soluble in alcohol and dilute alkali solutions.

Contents

Thymol blue(pH indicator)
below pH 8.0above pH 9.6
8.09.6
Thymol blue(pH indicator)
below pH 1.2above pH 2.8
1.22.8

It transitions from red to yellow at pH 1.2–2.8 and from yellow to blue at pH 8.0–9.6. It is usually a component of Universal indicator.

At wavelength (378 - 382) nm, extinction coefficient > 8000 and at wavelength (298 - 302) nm , the extinction coefficient > 12000. [3]

Structures

Thymol blue has different structures at different pH.

Thymolblau.png thymol blue.
Color of thymol blue solution at different acid-base conditions: left: acidic, middle: neutral, right: alkaline Color change of thymol blue at different pH.jpg
Color of thymol blue solution at different acid-base conditions: left: acidic, middle: neutral, right: alkaline

Safety

It may cause irritation. Its toxicological properties have not been fully investigated. Harmful if swallowed, Acute Toxicity. Only Hazardous when percent values are above 10%. [4]

Bibliography

Related Research Articles

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Primary color Sets of colors that can be mixed to produce gamut of colors

A set of primary colors consists of colorants or colored lights that can be mixed in varying amounts to produce a gamut of colors. This is the essential method used to create the perception of a broad range of colors in, e.g., electronic displays, color printing, and paintings. Perceptions associated with a given combination of primary colors can be predicted by an appropriate mixing model that reflects the physics of how light interacts with physical media, and ultimately the retina.

Ultraviolet–visible spectroscopy Range of spectroscopic analysis

UV spectroscopy or UV–visible spectrophotometry refers to absorption spectroscopy or reflectance spectroscopy in part of the ultraviolet and the full, adjacent visible regions of the electromagnetic spectrum. This means it uses light in the visible and adjacent ranges. The absorption or reflectance in the visible range directly affects the perceived color of the chemicals involved. In this region of the spectrum, atoms and molecules undergo electronic transitions. Absorption spectroscopy is complementary to fluorescence spectroscopy, in that fluorescence deals with transitions of electrons from the excited state to the ground state, while absorption measures transitions from the ground state to the excited state.

Bromothymol blue pH indicator

Bromothymol blue is a pH indicator. It is mostly used in applications that require measuring substances that would have a relatively neutral pH. A common use is for measuring the presence of carbonic acid in a liquid. It is typically sold in solid form as the sodium salt of the acid indicator.

Spectrophotometry Deals with visible light, near-ultraviolet, and near-infrared, but does not cover time-resolved spectroscopic techniques

Spectrophotometry is a branch of electromagnetic spectroscopy concerned with the quantitative measurement of the reflection or transmission properties of a material as a function of wavelength. Spectrophotometry uses photometers, known as spectrophotometers, that can measure the intensity of a light beam at different wavelengths. Although spectrophotometry is most commonly applied to ultraviolet, visible, and infrared radiation, modern spectrophotometers can interrogate wide swaths of the electromagnetic spectrum, including x-ray, ultraviolet, visible, infrared, and/or microwave wavelengths.

Fluorophore Agents that emit light after excitation by light

A fluorophore is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with several π bonds.

Coomassie brilliant blue Chemical compound

Coomassie brilliant blue is the name of two similar triphenylmethane dyes that were developed for use in the textile industry but are now commonly used for staining proteins in analytical biochemistry. Coomassie brilliant blue G-250 differs from Coomassie brilliant blue R-250 by the addition of two methyl groups. The name "Coomassie" is a registered trademark of Imperial Chemical Industries.

Bromophenol blue Chemical compound

Bromophenol blue is used as a pH indicator, an electrophoretic color marker, and a dye. It can be prepared by slowly adding excess bromine to a hot solution of phenolsulfonphthalein in glacial acetic acid.

Thymol Chemical compound found in plants including thyme

Thymol (also known as 2-isopropyl-5-methylphenol, IPMP) is a natural monoterpenoid phenol derivative of p-Cymene, C10H14O, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris (common thyme), ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris.

Thymolphthalein Chemical compound

Thymolphthalein is a phthalein dye used as an acid–base (pH) indicator. Its transition range is around pH 9.3–10.5. Below this pH, it is colorless; above, it is blue. The molar extinction coefficient for the blue thymolphthalein dianion is 38,000 M−1 cm−1 at 595 nm.

Universal indicator Indicator that works over a wide range of pH

A universal indicator is a pH indicator made of a solution of several compounds that exhibits several smooth colour changes over a wide range pH values to indicate the acidity or alkalinity of solutions. Although there are several commercially available universal pH indicators, most are a variation of a formula patented by Yamada in 1933. Details of this patent can be found in Chemical Abstracts. Experiments with Yamada's universal indicator are also described in the Journal of Chemical Education.

Phenol red Chemical compound

Phenol red is a pH indicator frequently used in cell biology laboratories.

Chromophore Part of a molecule responsible for its color

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Cyanines, also referred to as tetramethylindo(di)-carbocyanines are defined as "synthetic dyes with the general formula R2N[CH=CH]nCH=N+R2↔R2N+=CH[CH=CH]nNR2 in which the nitrogen and part of the conjugated chain usually form part of a heterocyclic system, such as imidazole, pyridine, pyrrole, quinoline and thiazole." Cyanines are used in industry biotechnology.

Underwater vision Effects of the underwater environment on (human) vision

Underwater vision is the ability to see objects underwater, and this is significantly affected by several factors. Underwater, objects are less visible because of lower levels of natural illumination caused by rapid attenuation of light with distance passed through the water. They are also blurred by scattering of light between the object and the viewer, also resulting in lower contrast. These effects vary with wavelength of the light, and color and turbidity of the water. The vertebrate eye is usually either optimised for underwater vision or air vision, as is the case in the human eye. The visual acuity of the air-optimised eye is severely adversely affected by the difference in refractive index between air and water when immersed in direct contact. Provision of an airspace between the cornea and the water can compensate, but has the side effect of scale and distance distortion. The diver learns to compensate for these distortions. Artificial illumination is effective to improve illumination at short range.

Dansyl chloride Chemical compound

Dansyl chloride or 5-(DimethylAmino)Naphthalene-1-SulfonYL chloride is a reagent that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green–fluorescent sulfonamide adducts. It can also be made to react with secondary amines. Dansyl chloride is widely used to modify amino acids; specifically, protein sequencing and amino acid analysis. Dansyl chloride may also be denoted DNSC. Likewise, a similar derivative, dansyl amide is known as DNSA.

Brookers merocyanine Chemical compound

Brooker's merocyanine is an organic dye belonging to the class of merocyanines.

The near-infrared (NIR) window defines the range of wavelengths from 650 to 1350 nanometre (nm) where light has its maximum depth of penetration in tissue. Within the NIR window, scattering is the most dominant light-tissue interaction, and therefore the propagating light becomes diffused rapidly. Since scattering increases the distance travelled by photons within tissue, the probability of photon absorption also increases. Because scattering has weak dependence on wavelength, the NIR window is primarily limited by the light absorption of blood at short wavelengths and water at long wavelengths. The technique using this window is called NIRS. Medical imaging techniques such as fluorescence image-guided surgery often make use of the NIR window to detect deep structures.

Thiosulfate-citrate-bile salts-sucrose agar

Thiosulfate-citrate-bile salts-sucrose agar, or TCBS agar, is a type of selective agar culture plate that is used in microbiology laboratories to isolate Vibrio species. TCBS agar is highly selective for the isolation of V. cholerae and V. parahaemolyticus as well as other Vibrio species.Apart from TCBS other rapid testing dipsticks like Immunochromatographic dipstick is also used in endemic areas such as Asia, Africa and Latin America. Though, TCBS agar study is required for confirmation. This becomes immensely important in cases of gastroenteritis caused by campylobacter species, whose symptoms mimic that of cholera. Since no yellow bacterial growth is observed in case of Campylobacter species on TCBS Agar, chances of incorrect diagnosis can be rectified.TCBS agar contains high concentrations of sodium thiosulfate and sodium citrate to inhibit the growth of Enterobacteriaceae. Inhibition of Gram-positive bacteria is achieved by the incorporation of ox gall, which is a naturally occurring substance containing a mixture of bile salts and sodium cholate, a pure bile salt. Sodium thiosulfate also serves as a sulfur source and its presence, in combination with ferric citrate, allows for the easy detection of hydrogen sulfide production. Saccharose (sucrose) is included as a fermentable carbohydrate for metabolism by Vibrio species. The alkaline pH of the medium enhances the recovery of V. cholerae and inhibits the growth of others. Thymol blue and bromothymol blue are included as indicators of pH changes.

The molar attenuation coefficient is a measurement of how strongly a chemical species attenuates light at a given wavelength. It is an intrinsic property of the species. The SI unit of molar attenuation coefficient is the square metre per mole, but in practice, quantities are usually expressed in terms of M−1⋅cm−1 or L⋅mol−1⋅cm−1. In older literature, the cm2/mol is sometimes used; 1 M−1⋅cm−1 equals 1000 cm2/mol. The molar attenuation coefficient is also known as the molar extinction coefficient and molar absorptivity, but the use of these alternative terms has been discouraged by the IUPAC.

References

  1. 1 2 Thymol Blue
  2. "Thymol blue". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  3. "Product Specification: Thymol Blue- ACS reagent" (PDF). Sigma-Aldrich. 9 October 2017. p. 1.
  4. "Thymol blue". PubChem. Retrieved 2017-10-09.