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MedKoo Cat#: 591597 | Name: Orthocresol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ortho-Cresol, also 2-methylphenol, is an organic compound with the formula CH₃C₆H₄. It is a colourless solid that is widely used intermediate in the production of other chemicals.

Chemical Structure

Orthocresol
Orthocresol
CAS#95-48-7

Theoretical Analysis

MedKoo Cat#: 591597

Name: Orthocresol

CAS#: 95-48-7

Chemical Formula: C7H8O

Exact Mass: 108.0575

Molecular Weight: 108.14

Elemental Analysis: C, 77.75; H, 7.46; O, 14.79

Price and Availability

Size Price Availability Quantity
5g USD 240.00
100g USD 380.00
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Related CAS #
No Data
Synonym
Orthocresol; NSC 23076 NSC-23076; NSC23076
IUPAC/Chemical Name
Phenol, 2-methyl-
InChi Key
QWVGKYWNOKOFNN-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
SMILES Code
OC1=CC=CC=C1C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
o-Cresol is a widely used intermediate in the production of other chemicals.
In vitro activity:
This study analysed cell death induced by the herbicide dinitro-o-cresol (DNOC) in soybean (Glycine max) suspension cell cultures and evaluated biochemical and molecular events associated with programmed cell death. DNOC-treated cells showed fragmented nuclear DNA as assessed by an in situ assay that detects 3'-OH ends. Reference: J Plant Physiol. 2007 Jun;164(6):675-84. https://pubmed.ncbi.nlm.nih.gov/17223224/
In vivo activity:
This study evaluated the toxicological effects of o-cresol on differential gene expression profile of rat liver and prostate. Rats exposed to 15 g kg-1 of o-cresol showed a 16 % loss in body weight by the end of the study, which may have been related to o-cresol making feed unpalatable at this concentration. Liver and prostate tissue samples were collected at the end of the treatment. mRNA analysis revealed that apoptotic genes (CYP3A, COX-2, PPARγ, BAX, BCL2, AKT-1, and PKCα) related to cancer were up-regulated in liver and prostate tissues isolated from groups exposed to 5 g kg-1 and 15 g kg-1o-cresol in comparison to control. Reference: Arh Hig Rada Toksikol. 2011 Jun;62(2):121-9. https://pubmed.ncbi.nlm.nih.gov/21705299/

Preparing Stock Solutions

The following data is based on the product molecular weight 108.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Aranha MM, Matos AR, Teresa Mendes A, Vaz Pinto V, Rodrigues CM, Arrabaça JD. Dinitro-o-cresol induces apoptosis-like cell death but not alternative oxidase expression in soybean cells. J Plant Physiol. 2007 Jun;164(6):675-84. doi: 10.1016/j.jplph.2006.09.010. Epub 2007 Jan 16. PMID: 17223224. 2. Khalil WK, Booles HF. Protective role of selenium against over-expression of cancer-related apoptotic genes induced by o-cresol in rats. Arh Hig Rada Toksikol. 2011 Jun;62(2):121-9. doi: 10.2478/10004-1254-62-2011-2074. PMID: 21705299.
In vitro protocol:
1. Aranha MM, Matos AR, Teresa Mendes A, Vaz Pinto V, Rodrigues CM, Arrabaça JD. Dinitro-o-cresol induces apoptosis-like cell death but not alternative oxidase expression in soybean cells. J Plant Physiol. 2007 Jun;164(6):675-84. doi: 10.1016/j.jplph.2006.09.010. Epub 2007 Jan 16. PMID: 17223224.
In vivo protocol:
1. Khalil WK, Booles HF. Protective role of selenium against over-expression of cancer-related apoptotic genes induced by o-cresol in rats. Arh Hig Rada Toksikol. 2011 Jun;62(2):121-9. doi: 10.2478/10004-1254-62-2011-2074. PMID: 21705299.
1: Huţanu CA, Zaharia M, Pintilie O. Quenching of tryptophan fluorescence in the presence of 2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and their mechanism of toxicity. Molecules. 2013 Feb 18;18(2):2266-80. doi: 10.3390/molecules18022266. PubMed PMID: 23429343. 2: Yamasaki M, Makihara N, Hazama R, Morita H, Yamada H. PP094. A comparison of gestational changes in urinary excretion of magnesium with those of calcium. Pregnancy Hypertens. 2012 Jul;2(3):291. doi: 10.1016/j.preghy.2012.04.205. Epub 2012 Jun 13. PubMed PMID: 26105416. 3: Seko Y, Shimokawa H, Pang J, Tokoro T. Disturbance of electrolyte balance in vitreous of chicks with form-deprivation myopia. Jpn J Ophthalmol. 2000 Jan-Feb;44(1):15-9. PubMed PMID: 10698020. 4: Zavalic M, Mandic Z, Turk R, Bogadi-Sare A, Plavec D, Gomzi M, Skender LJ. Assessment of colour vision impairment in male workers exposed to toluene generally above occupational exposure limits. Occup Med (Lond). 1998 Apr;48(3):175-80. PubMed PMID: 9659727. 5: Zavalić M, Mandić Z, Turk R, Bogadi-Sare A, Plavec D, Skender LJ. Qualitative color vision impairment in toluene-exposed workers. Int Arch Occup Environ Health. 1998 May;71(3):194-200. PubMed PMID: 9591161. 6: Zavalić M, Mandić Z, Turk R, Bogadi-Sare A, Plavec D. Quantitative assessment of color vision impairment in workers exposed to toluene. Am J Ind Med. 1998 Mar;33(3):297-304. PubMed PMID: 9481429. 7: Luqman AK, Amin M. A kinetic scheme for the early phase of ATP hydrolysis by actomyosin ATPase and its bioenergetic implications. Indian J Biochem Biophys. 1995 Feb;32(1):37-43. PubMed PMID: 7665193. 8: Yamazaki K, Tanaka E, Shimojo N, Honda K, Yamamoto R, Misawa S. [Locomotor activity and urinary excretion of orthocresol in rats exposed to toluene]. Nihon Hoigaku Zasshi. 1990 Jun;44(3):234-42. Japanese. PubMed PMID: 2232334. 9: Baelum J. Toluene in alveolar air during controlled exposure to constant and to varying concentrations. Int Arch Occup Environ Health. 1990;62(1):59-64. PubMed PMID: 2295523. 10: Døssing M, Aelum JB, Hansen SH, Lundqvist GR, Andersen NT. Urinary hippuric acid and orthocresol excretion in man during experimental exposure to toluene. Br J Ind Med. 1983 Nov;40(4):470-3. PubMed PMID: 6626478; PubMed Central PMCID: PMC1009223. 11: Esquevin H, Mirouze D, Raynaud A, Michel H, Cadi N, Loriot J. [Acute hepatonephritis caused by dinitro-orthocresol]. Nouv Presse Med. 1981 Jun 27;10(28):2371-2. French. PubMed PMID: 7267344. 12: Kleĭner AI, Sonkin IS. [Clinical aspects of acute combined intoxication with dinitro-orthocresol (DINOC) and carbolineum]. Vrach Delo. 1977 Apr;(4):126-8. Russian. PubMed PMID: 860486. 13: Duchassaing D, Ekindjian OG, Leluan G. [Automated method for determining calcium in biological liquids]. Ann Biol Clin (Paris). 1977;35(2):133-8. French. PubMed PMID: 921011. 14: Markićević A, Prpić-Majić D, Bosnar-Turk N. [Results of examination of workers exposed to dinitro-orthocresol (DNOC)]. Arh Hig Rada Toksikol. 1972;23(1):1-9. Croatian. PubMed PMID: 4655245. 15: Dalhamn T. Ciliostatic effect of orthocresol and metacresol. Arch Otolaryngol. 1968 Feb;87(2):162-4. PubMed PMID: 5635356. 16: Truhaut R, De Lavaur E. [Study of the metabolism of dinitro-4,6-orthocresol in the rabbit]. C R Acad Sci Hebd Seances Acad Sci D. 1967 Apr 10;264(15):1937-40. French. PubMed PMID: 4963844. 17: BURKATSKAIA EN. [ESTABLISHMENT OF THE MAXIMUM PERMISSIBLE CONCENTRATION OF DINITRO-ORTHOCRESOL IN THE AIR]. Gig Sanit. 1965 Feb;30:34-7. Russian. PubMed PMID: 14268468. 18: VAINTRAUB FP. [POLAROGRAPHIC DETERMINATION OF DINITRO-ORTHOCRESOL (ON LEAVES, TWIGS AND IN SOIL)]. Vopr Pitan. 1964 May-Jun;23:75-9. Russian. PubMed PMID: 14204734. 19: WASSERMANN M, MIHAIL G, ILIESCU S, VANCEA G, SAVA V, IOSUBAS S. [Working conditions and state of health of agricultural insect exterminators handling dinitro-orthocresol during the winter]. Concours Med. 1960 May 14;82:2537-44. French. PubMed PMID: 13843043. 20: ZELDENRUST J. [Dinitro-orthocresol poisoning]. Ned Tijdschr Geneeskd. 1956 Oct 13;100(41):2964-5. Dutch. PubMed PMID: 13387831.

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GE-2270 A

GE-2270 A