Indole-3-pyrubate

Modify Date: 2024-01-02 12:46:42

Indole-3-pyrubate Structure
Indole-3-pyrubate structure
Common Name Indole-3-pyrubate
CAS Number 392-12-1 Molecular Weight 203.194
Density 1.4±0.1 g/cm3 Boiling Point 445.2±28.0 °C at 760 mmHg
Molecular Formula C11H9NO3 Melting Point 215 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 223.0±24.0 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Indole-3-pyrubate


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].

 Names

Name 3-(indol-3-yl)pyruvic acid
Synonym More Synonyms

 Indole-3-pyrubate 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
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

 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
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

 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%

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 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
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