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Safety Information

SMB00206

Sigma-Aldrich

Paulownin

≥95% (LC/MS-ELSD)

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About This Item

Empirical Formula (Hill Notation):
C20H18O7
CAS Number:
13040-46-5
Molecular Weight:
370.35
MDL number:
MFCD20261059
UNSPSC Code:
12352205
PubChem Substance ID:
329824868
NACRES:
NA.25

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

O[C@]12CO[C@@H]([C@H]1CO[C@@H]2c3ccc4OCOc4c3)c5ccc6OCOc6c5

InChI

1S/C20H18O7/c21-20-8-23-18(11-1-3-14-16(5-11)26-9-24-14)13(20)7-22-19(20)12-2-4-15-17(6-12)27-10-25-15/h1-6,13,18-19,21H,7-10H2/t13-,18-,19-,20-/m1/s1

InChI key

CAQZFLPWHBKTTR-WNISUXOKSA-N

Related Categories

General description

Natural product derived from plant source.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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F Ishibashi et al.
Bioscience, biotechnology, and biochemistry, 65(1), 29-34 (2001-03-29)
Short enantiomeric syntheses of the 1-hydroxy/acetoxy-3,7-dioxabicyclo[3.3.0]octane lignans, paulownin, and (+)-phrymarin I and II, were accomplished by starting from the chiral synthon, (R)-(+)-3-hydroxybutanolide, and employing photocyclization as the key step.
Steven R Angle et al.
The Journal of organic chemistry, 73(16), 6268-6278 (2008-07-24)
A formal [3 + 2]-cycloaddition involving the Lewis acid mediated reaction of alpha-silyloxy aldehydes and styrenes to afford 3-alkyl-2-aryltetrahydrofuran-4-ols has been developed. This methodology was applied to the total synthesis of the naturally occurring furofuran lignan (+/-)-paulownin.

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