Cat. No.: HY-W014701

1,4-Dihydroxy-2-naphthoic acid

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1,4-Dihydroxy-2-naphthoic acid is an aryl hydrocarbon receptor (AhR) agonist. 1,4-Dihydroxy-2-naphthoic acid is also a bacterially derived metabolite and has anti-inflammatory activity.

For research use only. We do not sell to patients.

Purity: 99.60%
CAS No.: 31519-22-9
Formula: C₁₁H₈O₄
Molecular Weight:204.18

Storage:

4°C, sealed storage, away from moisture

* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

1,4-Dihydroxy-2-naphthoic acid Chemical Structure

CAS No.: 31519-22-9

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- In Vitro
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

1,4-Dihydroxy-2-naphthoic acid is an aryl hydrocarbon receptor (AhR) agonist. 1,4-Dihydroxy-2-naphthoic acid is also a bacterially derived metabolite and has anti-inflammatory activity^[1].

All Cytochrome P450 Isoforms :

All Interleukin Related Isoforms :

In Vitro

1,4-Dihydroxy-2-naphthoic acid (25-1000 μM, 18-24 h) induces > 70% of the response for CYP1A1 and CYP1B1 in both YAMC and Caco2 cells^[2].
1,4-Dihydroxy-2-naphthoic acid (100 μM, 24 h) inhibits IL-1β, IL-6, IL-23, p19 and IL-17A mRNA levels in LPS (HY-D1056)-stimulated RAW264.7 cells^[4].
1,4-Dihydroxy-2-naphthoic acid (48-72 h) inhibits proliferation against HaCaT, NCTC 2544, Hs-69 and PIG1 cells with IC₅₀s of 38.94, 46,80, 226.3 and 23.98 μM at 72 h^[5].
1,4-Dihydroxy-2-naphthoic acid (15-120 μM, 9-72 h) induces apoptosis and causes G0/G1 Cell cycle arrest in HaCaT cells in time and dose dependent manners^[5].
1,4-Dihydroxy-2-naphthoic acid (30-240 μM, 24-48 h) decreases MMP, increases DNA fragmentation and causes nuclear translocation of AIF and endoG in HaCaT cells^[5].
1,4-Dihydroxy-2-naphthoic acid (20-100 μM, 72 h) exhibits relatively low skin irritation, that significantly induces the release of IL-1α only at a concentration of 60 μM in NCTC2544cells^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

RT-PCR^[2]

Cell Line:

YAMC and Caco2 cells
Concentration:

25, 50, 100, 250, 500, 1000 μM
Incubation Time:

18 h
Result:

Induced Cyp1a1 and Cyp1b1 in both cells.
Completely eliminated the induction effects on Cyp1a1 and Cyp1b1 when the AhR was knocked out.

Western Blot Analysis^[2]

Cell Line:

YAMC and Caco2 cells
Concentration:

500 μM
Incubation Time:

24 h
Result:

Induced Cyp1a1 and Cyp1b1 expression in both cells.

RT-PCR^[4]

Cell Line:

LPS-stimulated RAW264.7 cells
Concentration:

100 μM
Incubation Time:

24 h
Result:

Inhibited IL-1β, IL-6, IL-23p19 and IL-17A mRNA levels in RAW264.7 cells.

Apoptosis Analysis^[5]

Cell Line:

HaCaT cells
Concentration:

30, 60 and 120 μM
Incubation Time:

9, 24 and 72 h
Result:

Increased in nuclear fluorescence from dark blue to light blue/white (chromatin condensation) at 30 and 60 μM.
Formed apoptotic bodies at 120 μM.
Increased apoptosis ratio time dependently.
Activated Caspase-8 and Caspase-9 and cleavage PARP and Bid.

Apoptosis Analysis^[5]

Cell Line:

HaCaT cells
Concentration:

15, 30, 60 and 120 μM
Incubation Time:

24 h
Result:

Dose-dependently induced G0/G1 cell cycle arrest.
Upregulated p21, while downregulated Cyclin D1/D3 and Cdk4.

In Vivo

1,4-Dihydroxy-2-naphthoic acid (20 mg/kg, p.o., for 5-10 weeks) successfully prevents and reverses unpredictable chronic mild stress (UCMS)-induced anhedonia-like behavior in mice^[1].
1,4-Dihydroxy-2-naphthoic acid (2 mg/kg, p.o., for 14 days) reduces inflammation in mice with colitis by suppressing macrophage-derived proinflammatory cytokines^[4].
1,4-Dihydroxy-2-naphthoic acid (20 mg/kg, p.o., for 3 weeks) prevents mice motor dysfunction induced by MPTP (HY-W114750)^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

UCMS model established in female C57BL/6 mice (6-7 weeks)^[1]
Dosage:

20 mg/kg
Administration:

Oral administration (p.o.), once daily, 3 weeks prior to UCMS or 2 weeks after UCMS, for 5-10 weeks
Result:

Did not exhibit a reduction in sucrose preference.
Restored the activity of Ca-ATPase and glycogen levels, and reduced phospholipase and lipid peroxides.
Did not significantly affect open field test (OFT), marble bury (MB) and novelty-induced hypophagia (NIH) behaviors.
Had no significant effect on the light/dark (L/D) test or on anxiety behaviors in the elevated plus maze (EPM).
Had a significant effect on spatial learning in unstressed animals.

Animal Model:

Colitis model established in 8-week male interleukin-10-deficient mice^[4]
Dosage:

2 mg/kg
Administration:

Oral administration (p.o.) with water freely available, for 14 days
Result:

Significantly reduced the inflammation score.
Significantly reduced F4/80^⁺ cells and VCAM-1 expression.
Significantly inhibited IL-1β, IL-6, TNF-α, IL-23p19 and IL-17A mRNA levels.

Animal Model:

Parkinson's disease (PD) model established in male C57BL/6 mice^[6]
Dosage:

20 mg/kg
Administration:

Oral administration (p.o.), for 3 weeks
Result:

Prevented MPTP-induced deficits in the motor pole test and in the adhesive strip removal test.
Improved balance beam performance and completely prevented MPTP-induced reduction in stride length.

Chemical Information

CAS No. 31519-22-9
Appearance Solid
Molecular Weight 204.18
Formula C₁₁H₈O₄
Color Gray to brown
SMILES

OC1=CC(C(O)=O)=C(O)C2=CC=CC=C21
Structure Classification
- Ketones, Aldehydes, Acids
Initial Source

Propionibacterium freudenreichii
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

4°C, sealed storage, away from moisture

* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

Solvent & Solubility

In Vitro:

DMSO : 175 mg/mL (857.09 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

4.8976 mL

24.4882 mL

48.9764 mL

5 mM

0.9795 mL

4.8976 mL

9.7953 mL

10 mM

0.4898 mL

2.4488 mL

4.8976 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (286 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Madison CA, et al. 3,3'-Diindolylmethane and 1,4-dihydroxy-2-naphthoic acid prevent chronic mild stress induced depressive-like behaviors in female mice. J Affect Disord. 2022 Jul 15;309:201-210. [Content Brief]

[2]. Cheng Y, et al. Editor's Highlight: Microbial-Derived 1,4-Dihydroxy-2-naphthoic Acid and Related Compounds as Aryl Hydrocarbon Receptor Agonists/Antagonists: Structure-Activity Relationships and Receptor Modeling. Toxicol Sci. 2017 Feb;155(2):458-473. [Content Brief]

[3]. Kang JE, et al. A Novel Lactobacillus casei LP1 Producing 1,4-Dihydroxy-2-Naphthoic Acid, a Bifidogenic Growth Stimulator. Prev Nutr Food Sci. 2015 Mar;20(1):78-81. [Content Brief]

[4]. Okada Y, et al. 1,4-Dihydroxy-2-naphthoic acid from Propionibacterium freudenreichii reduces inflammation in interleukin-10-deficient mice with colitis by suppressing macrophage-derived proinflammatory cytokines. J Leukoc Biol. 2013 Sep;94(3):473-80. [Content Brief]

[5]. Mok CF, et al. 1,4-dihydroxy-2-naphthoic Acid Induces Apoptosis in Human Keratinocyte: Potential Application for Psoriasis Treatment. Evid Based Complement Alternat Med. 2013;2013:792840. [Content Brief]

[6]. Madison CA, et al. 1,4-dihydroxy-2-naphthoic acid prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced motor function deficits. Behav Pharmacol. 2025 Feb 1;36(1):40-46. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	4.8976 mL	24.4882 mL	48.9764 mL	122.4410 mL
	5 mM	0.9795 mL	4.8976 mL	9.7953 mL	24.4882 mL
	10 mM	0.4898 mL	2.4488 mL	4.8976 mL	12.2441 mL
	15 mM	0.3265 mL	1.6325 mL	3.2651 mL	8.1627 mL
	20 mM	0.2449 mL	1.2244 mL	2.4488 mL	6.1220 mL
	25 mM	0.1959 mL	0.9795 mL	1.9591 mL	4.8976 mL
	30 mM	0.1633 mL	0.8163 mL	1.6325 mL	4.0814 mL
	40 mM	0.1224 mL	0.6122 mL	1.2244 mL	3.0610 mL
	50 mM	0.0980 mL	0.4898 mL	0.9795 mL	2.4488 mL
	60 mM	0.0816 mL	0.4081 mL	0.8163 mL	2.0407 mL
	80 mM	0.0612 mL	0.3061 mL	0.6122 mL	1.5305 mL
	100 mM	0.0490 mL	0.2449 mL	0.4898 mL	1.2244 mL

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1,4-Dihydroxy-2-naphthoic acid

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All Cytochrome P450 Isoforms

All Interleukin Related Isoforms

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

1,4-Dihydroxy-2-naphthoic acid Related Classifications

HY-W014701 Related Classifications