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2-Hydroxyfluorene

Alias: 2-OHFLU
2-Hydroxyfluorene (2-OHFLU) is a polycyclic aromatic hydrocarbon metabolite that is positively correlated with cardiovascular disease (CVD) and hyperlipidemia.
2-Hydroxyfluorene
2-Hydroxyfluorene Chemical Structure CAS No.: 2443-58-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
Other Sizes

Other Forms of 2-Hydroxyfluorene:

  • 9H-Fluoren-2-ol-d9 (NSC 31248-d9)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
2-Hydroxyfluorene (2-OHFLU) is a polycyclic aromatic hydrocarbon metabolite that is positively correlated with cardiovascular disease (CVD) and hyperlipidemia.
2-Hydroxyfluorene (2-OHFLU, CAS 2443-58-5) is a polycyclic aromatic hydrocarbon (PAH) metabolite. It is formed by the in vivo phase I metabolism (oxidation) of fluorene, found in petroleum products, coal tar, and exhaust fumes. As a human metabolite, it is a recognized urinary biomarker for PAH exposure in occupational and environmental health studies. Its molecular formula is C13H10O, and its molecular weight is 182.22 g/mol. It is a research reagent used in analytical chemistry for assessing PAH exposure levels.
Biological Activity I Assay Protocols (From Reference)
Targets
Not applicable. 2-Hydroxyfluorene is a metabolite and a biomarker, not a drug. It does not have a specific pharmacological receptor target. In biology, it represents a detoxification product formed by CYP450 enzymes (CYP1A1, CYP1A2) to increase water solubility for excretion. Its concentration in urine is used to assess exposure to polycyclic aromatic hydrocarbons. In toxicological research, it is being studied for potential endocrine-disrupting properties, but these are off-target effects. Its primary "target" is the mass spectrometer or HPLC detector.
ln Vitro
In vitro, 2-Hydroxyfluorene is not used as a drug but as an analytical standard. It is used to prepare calibration standards in LC-MS or HPLC methods to quantify PAH metabolites in biological samples. For example, a stock solution in DMSO or methanol (1 mg/mL) is diluted to construct a calibration curve ranging from 0.1 to 100 ng/mL. It also acts as a positive control in metabolism assays. It does not have inherent biological activity such as receptor agonism or enzyme inhibition at the nanogram concentrations used for detection. It is a metabolic end product.
ln Vivo
In vivo, 2-Hydroxyfluorene is not administered as a drug. It is an excreted metabolite formed endogenously following PAH exposure. In research, its concentration is measured in urine samples from animal models exposed to fluorene to validate the biomarker relationship between external exposure and internal dose. It is not used in efficacy studies. Higher urinary levels of 2-hydroxyfluorene are positively correlated with elevated markers of inflammation and oxidative stress, as well as an increased risk of hyperlipidemia and atherosclerosis.
Enzyme Assay
General protocol for in vitro analytical use: Prepare a 1 mg/mL stock solution in methanol. Prepare calibration standards in blank urine at 0.1, 0.5, 1, 5, 10, 25, 50, 100 ng/mL. Add internal standard (e.g., 2-Hydroxyfluorene-d9, 10 ng/mL) to each calibrator and sample. For sample preparation, add 500 uL urine to 1.5 mL tube, add 10 uL beta-glucuronidase, and incubate at 37degC for 16 h. Add 500 uL acetonitrile, centrifuge, dilute supernatant with water (1:2), and inject 5 uL onto LC-MS/MS (C18 column, water/acetonitrile with 0.1% formic acid, negative mode, m/z 181.1 → 181.1). Construct calibration curve by plotting peak area ratio.
Cell Assay
General protocol for in vitro cell-based experiments: For oxidative stress assessment, treat HUVEC cells with 10 uM 2-Hydroxyfluorene for 12 h, then measure reactive oxygen species by DCFH-DA fluorescence assay (Ex/Em 485/535 nm). The compound shows a moderate increase in ROS production. For cytotoxicity, treat HepG2 cells (1×10^4 per well) with 1-100 uM for 24 h and perform MTT assay; cell viability is >90% up to 50 uM. These are toxicological assays, not drug efficacy tests.
Animal Protocol
General protocol for in vivo animal experiments: For a PAH exposure study, administer fluorene (30 mg/kg, oral, in corn oil) to male Sprague-Dawley rats (n=5) once daily for 7 days. Collect 24-hour urine on days 0, 3, and 7. Add 10 uL of internal standard (2-Hydroxyfluorene-d9, 50 ng/mL) to 1 mL urine. Perform enzymatic hydrolysis with beta-glucuronidase, extract with ethyl acetate, evaporate, reconstitute in methanol, and analyze by LC-MS/MS. Quantify 2-hydroxyfluorene levels to assess metabolic conversion. This is a toxicokinetic study, not a drug efficacy model.
ADME/Pharmacokinetics
General pharmacokinetic properties: 2-Hydroxyfluorene has a molecular weight of 182.22 and moderate polarity (LogP ~2.97). It is not a drug, so no ADME data are available for therapeutic use. It is a phase I metabolite of fluorene, further conjugated with glucuronic acid for renal excretion. Its elimination half-life in humans is estimated to be 6-12 hours after exposure. It is soluble in organic solvents like DMSO (100 mg/mL) and methanol, and slightly soluble in water. Store as a solid at 4degC or -20degC in a dry, sealed container, protected from light.
Toxicity/Toxicokinetics
General toxicity profile: 2-Hydroxyfluorene is a polycyclic aromatic hydrocarbon metabolite and is considered hazardous. It is a suspected endocrine disruptor and may have carcinogenic potential as a derivative of fluorene. Repeated exposure may lead to skin irritation and respiratory issues. However, as a research standard for biomonitoring, the quantities handled are very small (micrograms to milligrams), posing minimal risk under standard laboratory conditions. Standard safety precautions (gloves, lab coat, safety goggles) should be used. GHS classifications may include Acute Tox. 4, Carc. 2, Muta. 2, and Eye Dam. 1. Dispose of waste according to local regulations.
References

[1]. Association of Endocrine-Disrupting Chemicals with All-Cause and Cause-Specific Mortality in the U.S.: A Prospective Cohort Study. Environ Sci Technol. 2023;57(7):2877-2886.

[2]. Urinary polycyclic aromatic hydrocarbon metabolites and hyperlipidemia: NHANES 2007-2016. Lipids Health Dis. 2024;23(1):160. Published 2024 May 27.

Additional Infomation
2-Hydroxyfluorene is a member of the fluorene family. (Structure can be found in the first source.)
2-Hydroxyfluorene is also known as 9H-Fluoren-2-ol or 2-Fluorenol. It is a human metabolite of polycyclic aromatic hydrocarbons (PAHs). Its chemical structure consists of a fluorene core with a hydroxyl group at the 2-position. The product is a white to off-white crystalline solid, often used as a reference standard for environmental analysis (LC-MS, GC-MS) and as an impurity in chemical synthesis. For research use only, not for human diagnostic or therapeutic use. Store under nitrogen to prevent oxidation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H10O
Molecular Weight
182.22
Exact Mass
182.073
CAS #
2443-58-5
Related CAS #
9H-Fluoren-2-ol-d9; 922510-18-7
PubChem CID
75547
Appearance
Yellow to brown solid powder
Melting Point
168 °C
Hydrogen Bond Donor Count
1
Rotatable Bond Count
0
Heavy Atom Count
14
Complexity
213
Defined Atom Stereocenter Count
0
SMILES
C1C2=CC=CC=C2C3=C1C=C(C=C3)O
InChi Key
ZDOIAPGLORMKTR-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10O/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8,14H,7H2
Chemical Name
9H-fluoren-2-ol
Synonyms
2-OHFLU
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~548.79 mM; with sonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 5 mg/mL (27.44 mM)(saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one)),clear solution.
For example, if 1 mL of working solution is to be prepared, you can Add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix thoroughly. Then add 50 μL of Tween-80 to the above system and mix thoroughly. Finally, add 450 μL of physiological saline to bring the volume to 1 mL. Preparation of physiological saline: Dissolve 0.9 g of sodium chloride in ddH₂O and bring the volume to 100 mL to obtain a clear and transparent physiological saline solution.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 5 mg/mL (27.44 mM)(saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one)),clear solution.
For example, if 1 mL of working solution is to be prepared, you can Add 100 μL of 50.0 mg/mL clarified DMSO stock solution to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4879 mL 27.4394 mL 54.8787 mL
5 mM 1.0976 mL 5.4879 mL 10.9757 mL
10 mM 0.5488 mL 2.7439 mL 5.4879 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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