4-Hydroxybenzyl alcohol CAS#: 623-05-2; ChemWhat Code: 66883

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name4-Hydroxybenzyl alcohol
IUPAC Name4-(hydroxymethyl)phenol
Molecular StructureStructure of 4-hydroxybenzyl alcohol (PHBA) CAS 623-05-2
CAS Registry Number 623-05-2
EINECS Number210-768-0
MDL NumberMFCD00004658
Beilstein Registry Number1858967
Synonyms(4-hydroxyphenyl)methanol, 4-Hydroxybenzyl alcohol; CAS No.: 623-05-2
Molecular FormulaC7H8O2
Molecular Weight124.137
InChIInChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
InChI KeyBVJSUAQZOZWCKN-UHFFFAOYSA-N
Canonical SMILESc1cc(ccc1CO)O
Patent Information
Patent IDTitlePublication Date
CN109384644A method of synthesis of primary alcohol (by machine translation)2019
CN108456178With the neuroprotective activity of Rhizoma Chuanxiong hydrochlorothizide substituted P-hydroxy-methanol analogs derivatives (LQC – F) and its application (by machine translation)2018
CN107253894Halogenated aromatic compound hydroxylated method (by machine translation)2017
US2013/79532PROCESS FOR THE PREPARATION OF 2-HYDROXY-4-PHENYL-3,4-DIHYDRO-2H-CHROMEN-6-YL-METHANOL AND (R)-FESO-DEACYL2013
US2014/135524PERFLUOROPOLYVINYL MODIFIED ARYL INTERMEDIATES/MONOMERS2014

Physical Data

AppearanceWhite to off-white to yellow to cream colored crystalline powder
SolubilitySoluble in water (6.7 mg/ml at 20°C), dioxane (100 mg/ml), 1N NaOH (50 mg/ml), DMSO, and methanol.
Flash Point251-253°C
Refractive index1.5035 (estimate)
SensitivityLight Sensitive/Air Sensitive
Melting Point, °C Solvent (Melting Point)
120 – 122
118 – 119
110 – 112
119 – 123
43
125 – 126methanol
125benzene, ethanol
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C
1.14425
1.24-190
1.24
Description (Association (MCS))Partner (Association (MCS))
Adsorptiontitanium(IV) oxide

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Spectrum1Hchloroform-d1400
Chemical shifts, Spectrum1Hdimethylsulfoxide-d6400
Chemical shifts1Hwater-d2400
Chemical shifts, Spectrum13Cd(4)-methanol100
Spectrum1Hdimethylsulfoxide-d6
Spin-spin coupling constantsD2O, CD3CN
NMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Bandspotassium bromidefilm
Spectrumpotassium bromide
BandsKBr3360 – 1515 cm**(-1)
IR
Spectrumnujol1053 – 690 cm**(-1)
Description (Mass Spectrometry)
liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), time-of-flight mass spectra (TOFMS), spectrum
electrospray ionisation (ESI), spectrum
liquid chromatography mass spectrometry (LCMS), tandem mass spectrometry, electrospray ionisation (ESI), IT (ion trap), spectrum
liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), spectrum
spectrum, electron impact (EI)
high resolution mass spectrometry (HRMS), electrospray ionisation (ESI), spectrum
gas chromatography mass spectrometry (GCMS), spectrum
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Spectrumwater
Absorption maximaethanol225, 277, 2838511, 1549, 1318
H2Oin the presence of inorganic compounds273
Absorption maximaaq. NaOH275
UV/VIS
Description (Fluorescence Spectroscopy)
Spectrum, Maxima
Fluorescence

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 4-Hydroxybenzyl alcohol CAS 623-05-2
Route of Synthesis (ROS) of 4-Hydroxybenzyl alcohol CAS 623-05-2
ConditionsYield
With potassium carbonate In acetone for 4h; Heating;96%
With sodium hydride In N,N-dimethyl-formamide at 0 – 20℃; for 6h; Inert atmosphere;93%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;90%
Stage #1: (4-hydroxyphenyl)methanol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 20h;
87%
With sodium hydride 1.) DMF, RT, 1 h, 2.) DMF, RT, 6 h; Yield given. Multistep reaction;

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH315 (29.09%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (27.88%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNONH for all modes of transport
Under the room temperature and away from light
HS Code290729
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD
Druglikeness
Lipinski rules component
Molecular Weight124.139
logP0.805
HBA1
HBD2
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)40.46
Rotatable Bond (RotB)1
Matching Veber Rules2
Bioactivity
In vitro: Efficacy
Quantitative Results
pXParameterValue (qual)Value (quant)UnitEffect
5.52current density decrease(M-type K+ current (IK(M)) taken from -50 to -10 mV)Active
5.25Ki (inhibition constant)5.6µMantibiotic agent
5.21Ki (inhibition constant)6.1µM
5.11IC507.7µMantiproliferative agent
5.07Ki (inhibition constant)8.6μMantibiotic agent
4.93Ki (inhibition constant)10.5μMantibiotic agent
4.92Kd (dissociation constant)(at -50 to -10 mV)11.9μMantifungal agent
4.62inhibition percentage(cell death)80.8%neuroprotective agent
4protein expression level decreaseActiveμg/mlantifungal agent
Quantitative Results
1 of 10Biological materialhuman
skin
Assay DescriptionPermeability coefficient of the compound in human skin was determined
MeasurementPermeability coefficient
2 of 10 Biological materialrat
Assay DescriptionDose of the compound required to inhibit arachidonic acid-induced increase in the ear thickness in rats measured 40 min after induction of inflammation
ResultsDose not calculated
MeasurementDose
3 of 10Assay DescriptionPartition coefficient of the compound in Octanol-water medium
4 of 10Biological materialAnura
skin
Assay DescriptionRelative biological activity of compound determined in frog skin as compared to that of 2-hydroxybenzyl alcohol
Resultslog RBR not calculated
Measurementlog RBR
5 of 10 Target4-cresol dehydrogenase [hydroxylating] flavoprotein subunit:Wild
Assay DescriptionSpecific activity of compound towards p-Cresol methylhydroxylase (PCMH) from denitrifying bacterial isolate (PC-07) using 100 umol 2,6-dichlorophenol-indophenol (DCPIP) upon incubation in 50 mM Tris-HCl buffer, pH 7.6 by colorimetric DCPIP-PMS assay; One unit is equivalent to 1.0 umol of DCPIP reduced per min per mg of protein
ResultsSpecific activity not calculated
MeasurementSpecific activity
6 of 10Assay DescriptionApparent partition coefficient (LogP) value of the compound was determined
MeasurementPartition coefficient
7 of 10EffectCytotoxic
Assay DescriptionTarget : Vitis vinifera cv. Chasselas cells
Bioassay : minimal NOVER-MSMO medium; incubated for 24 h at 24 deg C; cell death and membrane integrity assessed using vital dye neutral red; accumulation of dye in vacuoles and plasmolysis observed by light microscopy
8 of 10Target4-aminobutyrate aminotransferase, mitochondrial:Wild
Assay DescriptionEffect : enzyme; inhib. of
Bioassay : valproic acid (known anticonvulsant) used as reference comp. γ-aminobutyric acid; α-ketoglutaric acid; assay buffer, pH 8.0; 37 deg C; incubated for 30 min; NADP added and amount of NADPH generated for 20 min measured at 340 nm as activity of enzyme
Resultstitle comp. inhibited enzyme activity by 30.87 percent (vs. 65.38 percent inhibition for valproic acid)
9 of 10EffectPhytotoxic
Biological materialcucumber
Assay DescriptionBioassay : root elongation half inhibition concentration (RC50) was investigated after 48 h of incubation in the dark at 25 +/- 1 deg C, the root elongation of each seed was measured to 1 mm
ResultsRC50 309.0 mg/l
10 of 10EffectGermination Effect
Biological materialcucumber
Assay DescriptionBioassay : GC50: negative logarithm of germination rate 50 percent inhibition concentration in mol/l seeds purchased commercially; 100×15 mm disposable petri dishes; Whatman No. 1 filter paper; incubation time 48 h; 25 deg C; in the dark; pH 6.15; OECD, 1984
ResultsGC50 3.20 dimensionless
Toxicity/Safety Pharmacology
Quantitative Results
pXParameterValue (qual)Value (quant)UnitEffect
5MIC10.1µM
3percentage increase(of cellular protection)Activecytoprotective agent
2.7IC502mMantiproliferative agent
2.66IC502.2mMantiproliferative agent
inhibition percentage(of oxidized DCFH-DA to fluorescent DCF)ModerateCytotoxic
1 of 2EffectToxic
Biological materialTetrahymena pyriformis
Assay DescriptionEffect : growth
Bioassay : spectrophotometric, 540 nm; sterile medium; 27 deg C; pH 7.35; starting conc. of cells: ca. 2500 cells/ml; conc. of title comp.: saturated solution
2 of 2EffectCytotoxic
Assay DescriptionTarget : murine macrophage RAW264.7 cells
Bioassay : controls: cells incub. in absence of title comp.; MTT: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cells incub. with title comp. then treated with MTT for 2 h; cell viability determ. by MTT reduction assay
Use Pattern
4-Hydroxybenzyl alcohol CAS#: 623-05-2 Agricultural use
4-Hydroxybenzyl alcohol CAS#: 623-05-2 controlling nematodes
4-Hydroxybenzyl alcohol CAS#: 623-05-2 in combination with 2-Methyl-2-(methylthio)propanal O- (N-methylcarbamoyl)oxime, 2,2-Dimethyl-2,3-dihydro-l-benzofuran-7-yl methylcarbamate, Methyl 2- (dimethylamino)-N-[(methylcarbamoyl)oxy]-2-oxoethanimidothioate, 2-Methyl-2- (methylsulfonyl)propionaldehyde 0-(methylcarbamoyl)oxime, Ο,Ο-Diethyl 0-[4- (methylsulfinyl)phenyl] phosphorothioate, l-(ethoxy-propylsulfanylphosphoryl)sulfanylpropane, (RS)-N-[Ethoxy-(3-methyl-4-methylsulfanylphenoxy)phosphoryl]propan-2-amine, Streptomyces lydicus WYEC
4-Hydroxybenzyl alcohol CAS#: 623-05-2 in combination with Sinapsis alba plant extract, Sinapsis alba seed meal, or a combination thereof
4-Hydroxybenzyl alcohol CAS#: 623-05-2 in combination with potato hatching factor, a potato root diffusate, a tomato root diffusate, a soybean root diffusate, a sugar beet root diffusate, or any combination thereof
4-Hydroxybenzyl alcohol CAS#: 623-05-2 therapeutic component of pharmaceutical compoosition

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