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(-)-Sinoacutine

$182

  • Brand : BIOFRON

  • Catalogue Number : AV-H17082

  • Specification : 98%

  • CAS number : 4090-18-0

  • Formula : C19H21NO4

  • Molecular Weight : 327.37

  • PUBCHEM ID : 821366

  • Volume : 20mg

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Catalogue Number

AV-H17082

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

327.37

Appearance

Powder

Botanical Source

Alkaloid from Sinomenium acutum, Corydalis spp., Nandina spp. and others in the Menispermaceae, Papaveraceae and Lauraceae

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CCC23C=C(C(=O)C=C2C1CC4=C3C(=C(C=C4)OC)O)OC

Synonyms

(9α,13α)-4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one/4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one/Salutaridine/5,6,8,14-Tetradehydro-4-hydroxy-3,6-dimethoxy-17-methylmorphinan-7-one/Morphinan-7-one, 5,6,8,14-tetradehydro-4-hydroxy-3,6-dimethoxy-17-methyl-, (9α,13α)-/Salutarine/Sinoacutine/Floripavine/Morphinan-7-one, 5,6,8,14-tetradehydro-4-hydroxy-3,6-dimethoxy-17-methyl-

IUPAC Name

(1R,9S)-3-hydroxy-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaen-12-one

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

275.8±30.1 °C

Boiling Point

532.5±50.0 °C at 760 mmHg

Melting Point

198℃

InChl

InChI=1S/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m0/s1

InChl Key

GVTRUVGBZQJVTF-ORAYPTAESA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:4090-18-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

26272907

Abstract
Opioids are the primary drugs used in Western medicine for pain management and palliative care. Farming of opium poppies remains the sole source of these essential medicines, despite diverse market demands and uncertainty in crop yields due to weather, climate change, and pests. We engineered yeast to produce the selected opioid compounds thebaine and hydrocodone starting from sugar. All work was conducted in a laboratory that is permitted and secured for work with controlled substances. We combined enzyme discovery, enzyme engineering, and pathway and strain optimization to realize full opiate biosynthesis in yeast. The resulting opioid biosynthesis strains required the expression of 21 (thebaine) and 23 (hydrocodone) enzyme activities from plants, mammals, bacteria, and yeast itself. This is a proof of principle, and major hurdles remain before optimization and scale-up could be achieved. Open discussions of options for governing this technology are also needed in order to responsibly realize alternative supplies for these medically relevant compounds. Copyright ? 2015, American Association for the Advancement of Science.
Title

Complete biosynthesis of opioids in yeast.

Author

Galanie S1, Thodey K2, Trenchard IJ2, Filsinger Interrante M2, Smolke CD3.

Publish date

2015 Sep 4

PMID

26147354

Abstract
The gateway to morphine biosynthesis in opium poppy (Papaver somniferum) is the stereochemical inversion of (S)-reticuline since the enzyme yielding the first committed intermediate salutaridine is specific for (R)-reticuline. A fusion between a cytochrome P450 (CYP) and an aldo-keto reductase (AKR) catalyzes the S-to-R epimerization of reticuline via 1,2-dehydroreticuline. The reticuline epimerase (REPI) fusion was detected in opium poppy and in Papaver bracteatum, which accumulates thebaine. In contrast, orthologs encoding independent CYP and AKR enzymes catalyzing the respective synthesis and reduction of 1,2-dehydroreticuline were isolated from Papaver rhoeas, which does not accumulate morphinan alkaloids. An ancestral relationship between these enzymes is supported by a conservation of introns in the gene fusions and independent orthologs. Suppression of REPI transcripts using virus-induced gene silencing in opium poppy reduced levels of (R)-reticuline and morphinan alkaloids and increased the overall abundance of (S)-reticuline and its O-methylated derivatives. Discovery of REPI completes the isolation of genes responsible for known steps of morphine biosynthesis.
Title

Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.

Author

Farrow SC1, Hagel JM1, Beaudoin GA1, Burns DC2, Facchini PJ1.

Publish date

2015 Sep

PMID

24104569

Abstract
2013 Oct
Title

Morphine biosynthesis in opium poppy involves two cell types: sieve elements and laticifers.

Author

Onoyovwe A1, Hagel JM, Chen X, Khan MF, Schriemer DC, Facchini PJ.

Publish date

2013 Oct


Description :

(-)-Salutaridine (Salutaridine) is an alkaloid isolated from the stems of Sinomenium acutum[1].