Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Indole-3-pyruvic acid
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392-12-1

392-12-1 structure

Name: Indole-3-pyrubate
Chemical Name: 3-(indol-3-yl)pyruvic acid
CAS Number: 392-12-1
Molecular Formula: C₁₁H₉NO₃
Molecular Weight: 203.194
Catalog: Chemical reagent Organic reagent Bicyclic compound
Create Date: 2018-12-24 18:25:12
Modify Date: 2024-01-02 12:46:42
Indole-3-pyruvic acid, a keto analogue of tryptophan, is an orally active AHR agonist. Indole-3-pyruvic acid has antioxidant properties, and can be used in the research of inflammation, anxiety[1][2][3].

Name	3-(indol-3-yl)pyruvic acid
Synonyms	MFCD00005640 1H-Indole-3-propanoic acid, α-oxo- 3-(1H-Indol-3-yl)-2-oxopropanoic acid Indole pyruvic acid EINECS 206-874-1 Indole-3-pyrubate Indole-3-pyruvic acid INDOLE-3-PYRUVATE

Description	Indole-3-pyruvic acid, a keto analogue of tryptophan, is an orally active AHR agonist. Indole-3-pyruvic acid has antioxidant properties, and can be used in the research of inflammation, anxiety[1][2][3].
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Aryl Hydrocarbon Receptor Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease
Target	Microbial Metabolite
In Vitro	Indole-3-pyruvic acid (50 and 250 μM, 24 h) activates AHR in HepG2 cells[1]. Indole-3-pyruvic acid (50 μM, 4 days) does not inhibit Th1 cell differentiation but promotes Tr1 differentiation[1]. Indole-3-pyruvic acid (1 mM, 24 h) reduces UVB-induced cytotoxicity in HaCaT cells[1]. Indole-3-pyruvic acid (25 mM, 6 h) reduces the levels of COX-2 in HaCaT cells[2]. RT-PCR[2] Cell Line: HaCaT cells Concentration: 5-25 mM Incubation Time: 6 h Result: Inhibited UVB-stimulated mRNA expression of IL-1β, IL-6, and cyclooxygenase 2 (Cox-2).
In Vivo	Indole-3-pyruvic acid (oral administration, fed in MF chow (0.1%) for 5 d) activates AHR in BALB/c mice[1]. Indole-3-pyruvic acid (oral administration, fed in MF chow (0.1%) for 5 wk) abrogates chronic inflammation in a T cell-mediated colitis model[1]. Indole-3-pyruvic acid (100 μM, dose at skin) protects against UVB-induced skin damage in HR-1 hairless mice[2]. Indole-3-pyruvic acid (intraperitoneal injection, 100-200 mg/kg) increases the time spent in the open arms of the elevated plus maze in mice[3]. Animal Model: BALB/c mice[1] Dosage: Fed in MF chow.0.1% for 5 d Administration: Oral administration Result: Up-regulated the expression of Cyp1a1 (a biomarker for AHR activation) in the colon. Animal Model: T cell–mediated colitis model of SCID mice[1] Dosage: Fed in MF chow.0.1% for 5 wk Administration: Oral administration Result: Suppressed diarrhea and improved colon inflammation. Down-regulated the expression of Th1 and proinflammatory cytokines and upregulated the expression of IL-10 in the colon. Animal Model: HR-1 Hairless Mice[2] Dosage: 100 μM Administration: Dose at skin Result: Enhanced the epidermal thickness. Attenuated UVB-induced necrosis observed in upper layer of dermis.
References	[1]. Reiji Aoki, et al. Indole-3-Pyruvic Acid, an Aryl Hydrocarbon Receptor Activator, Suppresses Experimental Colitis in Mice. J Immunol. 2018 Dec 15;201(12):3683-3693. [2]. Reiji Aoki, et al. Protective effect of indole-3-pyruvate against ultraviolet b-induced damage to cultured HaCaT keratinocytes and the skin of hairless mice. PLoS One. 2014 May 8;9(5):e96804. [3]. I P Lapin, et al. Anxiolytic effect of indole-3-pyruvic acid (IPA) in mice. Pharmacol Res. 1993 Sep;28(2):129-34.

Density	1.4±0.1 g/cm3
Boiling Point	445.2±28.0 °C at 760 mmHg
Melting Point	215 °C (dec.)(lit.)
Molecular Formula	C₁₁H₉NO₃
Molecular Weight	203.194
Flash Point	223.0±24.0 °C
Exact Mass	203.058243
PSA	70.16000
LogP	0.46
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.685
Storage condition	2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM1880000

CHEMICAL NAME :: Indole-3-pyruvic acid

CAS REGISTRY NUMBER :: 392-12-1

BEILSTEIN REFERENCE NO. :: 0172966

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H9-N-O3

MOLECULAR WEIGHT :: 203.21

WISWESSER LINE NOTATION :: T56 BMJ D1VVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 500 ug/plate

REFERENCE :: JNCIAM Journal of the National Cancer Institute. (Washington, DC) V.1-60, 1940-78. For publisher information, see JJIND8. Volume(issue)/page/year: 57,921,1976

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H315-H319-H335
Precautionary Statements	P261-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi:Irritant;
Risk Phrases	R36/37/38
Safety Phrases	S26-S36-S24/25
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	NM1880000
HS Code	2918300090

Precursor 9
73-22-3 54753-57-0 54-12-6 79189-76-7
871023-09-5 1912-33-0 153-94-6 328-50-7
32817-17-7
DownStream 10
487-89-8 87-51-4 127-17-3 153-94-6
73-22-3 832-97-3 771-50-6 879-37-8
3050-37-1 150044-68-1

HS Code	2918300090
Summary	2918300090 other carboxylic acids with aldehyde or ketone function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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