Reticuline

Names

[ CAS No. ]:
485-19-8

[ Name ]:
Reticuline

[Synonym ]:
1-(3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Reticuline
1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol
2-Methyl-7-hydroxy-6-methoxy-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
1-(3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinol
Coclanoline
(±)-Reticuline
7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-

Biological Activity

[Description]:

Reticuline, isolated from Litsea cubeba, shows anti-inflammatory effects through JAK2/STAT3 and NF-κB signaling pathways. Reticuline inhibits mRNA expressions of TNF-α, and IL-6 and reduces the phosphorylation levels of JAK2 and STAT3[1].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT

Signaling Pathways >> JAK/STAT Signaling >> JAK

Signaling Pathways >> Epigenetics >> JAK

Signaling Pathways >> Stem Cell/Wnt >> JAK

Signaling Pathways >> JAK/STAT Signaling >> STAT

Research Areas >> Inflammation/Immunology

[Target]

JAK2

STAT3

NF-κB

[References]

[1]. Yang X, et al. Anti-Inflammatory Effects of Boldine and Reticuline Isolated from Litsea cubeba through JAK2/STAT3 and NF-κB Signaling Pathways. Planta Med. 2018 Jan;84(1):20-25.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
504.9±50.0 °C at 760 mmHg

[ Melting Point ]:
125-126ºC

[ Molecular Formula ]:
C₁₉H₂₃NO₄

[ Molecular Weight ]:
329.390

[ Flash Point ]:
259.2±30.1 °C

[ Exact Mass ]:
329.162720

[ PSA ]:
62.16000

[ LogP ]:
2.09

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
-20?C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NX5993000

CHEMICAL NAME :: 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((3-hydroxy-4-methoxyphenyl)meth yl)-6-methoxy-2-methy l-,(S)-

CAS REGISTRY NUMBER :: 485-19-8

BEILSTEIN REFERENCE NO. :: 4299976

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C19-H23-N-O4

MOLECULAR WEIGHT :: 329.43

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JNPRDF Journal of Natural Products. (Spahr & Glenn Co., 225 E. Spring St., Columbus, OH 43215) V.42- 1979- Volume(issue)/page/year: 42,399,1979

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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