(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one

Product Name: (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
CAS No.: 40456-50-6
Chemical Name: (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
Synonyms: Yatei;Yatein;(?)-Yatein;YatapoxvirusYatein;(+)-Deoxypodorhizon;(-)-Deoxypodorhizone;Yatein/deoxypodorhizone;(-)-trans-3-(3,4-Methylenedioxybenzyl)-2-(3,4,5-trimethoxybenzyl)butyrolactone;(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one;(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
CBNumber: CB22190075
Molecular Formula: C22H24O7
Formula Weight: 400.42
MOL File: 40456-50-6.mol

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(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Property

Boiling point:: 564.9±45.0 °C(Predicted)
Density: 1.266±0.06 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: Soluble in DMSO
form: A solid
color: Colorless to light yellow

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 29766
Product name: Yatein
Packaging: 500μg
Price: $153
Updated: 2024/03/01

Cayman Chemical

Product number: 29766
Product name: Yatein
Packaging: 1mg
Price: $290
Updated: 2024/03/01

AK Scientific

Product number: W1872
Product name: Yatein
Packaging: 1mg
Price: $421
Updated: 2021/12/16

Arctom

Product number: CFN98635
Product name: Yatein
Purity: ≥98%
Packaging: 5mg
Price: $463
Updated: 2021/12/16

Crysdot

Product number: CD32001467
Product name: Yatein
Purity: 95+%
Packaging: 5mg
Price: $730
Updated: 2021/12/16

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(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Chemical Properties,Usage,Production

Description

Yatein is a lignan that has been found in C. formosana and has diverse biological activities. It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC₅₀ = 1 μM). Yatein inhibits herpes simplex virus 1 (HSV-1) replication in a plaque reduction assay (IC₅₀ = 30.6 μM). It induces apoptosis and production of reactive oxygen species (ROS) in, and is cytotoxic to, A549 and CL1-5 non-small cell lung cancer (NSCLC) cells (IC₅₀s = 3.5 and 1.9 μM, respectively). Yatein inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in a concentration-dependent manner.

Uses

Yatein is a lignan isolated from A. chilensis, with antiproliferative activity[1]. Yatein suppresses herpes simplex virus type 1 (HSV-1 ) replication by interruption the immediate-early gene expression[2].

Definition

ChEBI: A member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively.

in vivo

Yatein (20 mg/kg; i.p.; five times per week; for 42 days) exhibits in vivo antitumor effects in a human lung adenocarcinoma xenograft mouse model^[3].

Animal Model:	Male NOD/SCID mice (6-8 weeks), with A549 cells xenograft^[3]
Dosage:	20 mg/kg
Administration:	Intraperitoneal injection, five times per week, for 42 days
Result:	Significantly slowed tumor growth and moderately increased both cyclin B1 expression and Cdc2 phosphorylation.

IC 50

HSV-1

References

[1] Donoso-Fierro C, et al. Antiproliferative activity of yatein isolated from Austrocedrus chilensis against murine myeloma cells: cytological studies and chemical investigations. Pharm Biol. 2015 Mar;53(3):378-85. DOI:10.3109/13880209.2014.922588
[2] Kuo YC, et al. Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 2006 Jul;70(3):112-20. DOI:10.1016/j.antiviral.2006.01.011
[3] Shang-Tse Ho, et al. Molecular Mechanisms Underlying Yatein-Induced Cell-Cycle Arrest and Microtubule Destabilization in Human Lung Adenocarcinoma Cells. Cancers (Basel). 2019 Sep; 11(9): 1384. DOI:10.3390/cancers11091384

(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Preparation Products And Raw materials

Raw materials

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(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Suppliers

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View Lastest Price from (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Yatein 40456-50-6
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥96%(HPLC)
Supply Ability: 10 g
Release date: 2020-05-12

40456-50-6, (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-oneRelated Search:

hydroxygenkwanin Artemether alpha-Terpineol alpha-Cyperone MOSLOFLAVONE Hydroxyecdysone 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one beta-Eudesmol (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one beta-Sitosterol

(-)-Deoxypodorhizone

(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one

(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-[(1,3-benzodioxole-5-yl)methyl]-4,5-dihydrofuran-2(3H)-one

(3R,4R)-3-(3,4,5-Trimethoxybenzyl)-4-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one

(3R,4R)-3-(3,4,5-Trimethoxybenzyl)-4-[(1,3-benzodioxol-5-yl)methyl]dihydrofuran-2(3H)-one

Yatein

(+)-Deoxypodorhizon

(3S)-3β-(3,4,5-Trimethoxybenzyl)-4α-[(1,3-benzodioxole-5-yl)methyl]-4,5-dihydrofuran-2(3H)-one

(3S)-4,5-Dihydro-3β-(3,4,5-trimethoxybenzyl)-4α-(1,3-benzodioxol-5-ylmethyl)furan-2(3H)-one

(-)-trans-3-(3,4-Methylenedioxybenzyl)-2-(3,4,5-trimethoxybenzyl)butyrolactone

YatapoxvirusYatein

2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-[(3,4,5-trimethoxyphenyl)methyl]-, (3R,4R)-

(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one

Yatein/deoxypodorhizone

Yatei

(?)-Yatein

(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one

40456-50-6