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Cat. No.: HY-N1356A

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(R)-Reticuline

(R)-Reticuline is a key intermediate and precursor in the biosynthetic pathway of morphinan alkaloids. (R)-Reticuline plays a central role in the metabolism of opium poppy (Papaver somniferum). (R)-Reticuline can either undergo O-methylation catalyzed by PSOMT1, or be converted to (+)-Salutaridine via regioselective and stereoselective oxidative coupling under the action of salutaridine synthase (CYP719B1). (R)-Reticuline serves as a direct precursor for the synthesis of important alkaloids such as morphine, codeine and thebaine.

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CAS No.: 3968-19-2
Formule: C₁₉H₂₃NO₄
Masse moléculaire:329.39

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4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

(R)-Reticuline Chemical Structure

CAS No.: 3968-19-2

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Description

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Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	>30 μM Compound: 6	Cytotoxicity against human A549 cells by SRB assay Cytotoxicity against human A549 cells by SRB assay	[PMID: 20594848]
HCT-15	IC₅₀	26.83 μM Compound: 6	Cytotoxicity against human HCT15 cells by SRB assay Cytotoxicity against human HCT15 cells by SRB assay	[PMID: 20594848]
SK-MEL-2	IC₅₀	>30 μM Compound: 6	Cytotoxicity against human SK-MEL-2 cells by SRB assay Cytotoxicity against human SK-MEL-2 cells by SRB assay	[PMID: 20594848]
SK-OV-3	IC₅₀	>30 μM Compound: 6	Cytotoxicity against human SKOV3 cells by SRB assay Cytotoxicity against human SKOV3 cells by SRB assay	[PMID: 20594848]

In Vitro

(R)-Reticuline (20 nmol; 60 min) is converted to salutaridine via a cytochrome P-450-dependent enzyme system by microsomal preparations from flowering stage Papaver somniferum capsules, with a K_m value of 17 μM for (R)-reticuline^[2].

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

Chemical Information

CAS No. 3968-19-2
Appearance Solid
Masse moléculaire 329.39
Formule C₁₉H₂₃NO₄
Color Off-white to light yellow
SMILES

OC1=CC2=C(C=C1OC)CCN(C)[C@@H]2CC3=CC=C(OC)C(O)=C3
Structure Classification
- Alkaloids
- Isoquinoline Alkaloids
Initial Source
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Pureté et documentation

Select Batch:

Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

Fiche technique (273 KB)
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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)
Instruction de manipulation (2659 KB)

Références

[1]. Ounaroon A, et al. (R, S)‐Reticuline 7‐O‐methyltransferase and (R, S)‐norcoclaurine 6‐O‐methyltransferase of Papaver somniferum–cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy[J]. The plant journal, 2003, 36(6): 808-819.

[2]. Gerardy R, et al. Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum[J]. Phytochemistry, 1992, 32(1): 79-86.

[3]. Cigan E, et al. Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis. Chem Sci. 2023;14(36):9863-9871. Published 2023 Aug 24. [Content Brief]

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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.

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(R)-Reticuline

Voir tous les produits spécifiques à Isoform Cytochrome P450