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Pinoresinol

CAT: 0804-HY-N6253-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6253-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].
CAS Number
487-36-5
Product Name Alternative
(+) -Pinoresinol
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis
Type
Natural Products
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/pinoresinol.html
Purity
99.48
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
COC1=C(O)C=CC([C@@H]2[C@]3([H])[C@]([C@@H](C4=CC(OC)=C(O)C=C4)OC3)([H])CO2)=C1
Molecular Formula
C20H22O6
Molecular Weight
358.39
Precautions
H302, H315, H319, H335
References & Citations
[1]Schroeder FC, et al. Pinoresinol: A lignol of plant origin serving for defense in a caterpillar. Proc Natl Acad Sci U S A. 2006 Oct 17;103 (42) :15497-501.|[2]Lee SR, et al. Accelerated degradation of cFLIPL and sensitization of the TRAIL DISC-mediated apoptotic cascade by pinoresinol, a lignan isolated from Rubia philippinensis. Sci Rep. 2019 Sep 18;9 (1) :13505.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

(+)-Pinoresinol

(+)-pinoresinol is an enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. It has a role as a hypoglycemic agent, a plant metabolite and a phytoestrogen.

CAS Number487-36-5
PubChem CID73399
IUPAC Name4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Molecular FormulaC20H22O6
Molecular Weight358.4
XLogP2.3
Topological Polar Surface Area77.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count26
Formal Charge0
Complexity431
SMILES
COC1=C(C=CC(=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC)O
InChI
InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
InChIKey
HGXBRUKMWQGOIE-AFHBHXEDSA-N
Chemical Structure
2D Structure
2D structure of (+)-Pinoresinol
CAS: 487-36-5
CID: 73399
Formula: C20H22O6
MW: 358.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight358.4
XLogP32.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass358.14163842
Monoisotopic Mass358.14163842
Topological Polar Surface Area77.4 Ų
Heavy Atom Count26
Formal Charge0
Complexity431
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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