Indole-3-pyrubate

Names

[ CAS No. ]:
392-12-1

[ Name ]:
Indole-3-pyrubate

[Synonym ]:
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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ 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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ 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%

Articles

Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K.

J. Med. Chem. 52 , 2786-93, (2009)

Human kynurenine aminotransferase I (hKAT I) catalyzes the formation of kynurenic acid, a neuroactive compound. Here, we report three high-resolution crystal structures (1.50-1.55 A) of hKAT I that ar...

A novel thiol-reductase activity of Arabidopsis YUC6 confers drought tolerance independently of auxin biosynthesis.

Nat. Commun. 6 , 8041, (2015)

YUCCA (YUC) proteins constitute a family of flavin monooxygenases (FMOs), with an important role in auxin (IAA) biosynthesis. Here we report that Arabidopsis plants overexpressing YUC6 display enhance...

Coordination of auxin and ethylene biosynthesis by the aminotransferase VAS1.

Nat. Chem. Biol. 9(4) , 244-6, (2013)

We identify an Arabidopsis pyridoxal-phosphate-dependent aminotransferase, VAS1, whose loss-of-function simultaneously increases amounts of the phytohormone auxin and the ethylene precursor 1-aminocyc...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.