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P1499

Sigma-Aldrich

Pterostilbene

≥97% (HPLC), solid

Synonym(s):

Pterocarpus marsupium, 3,5-Dimethoxy-4′-hydroxystilbene, 4-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]phenol

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About This Item

Empirical Formula (Hill Notation):
C16H16O3
CAS Number:
537-42-8
Molecular Weight:
256.30
MDL number:
MFCD00238710
UNSPSC Code:
12352200
PubChem Substance ID:
24724573
NACRES:
NA.77

Assay

≥97% (HPLC)

form

solid

storage condition

protect from light

solubility

DMSO: >20 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

COc1cc(OC)cc(\C=C\c2ccc(O)cc2)c1

InChI

1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

InChI key

VLEUZFDZJKSGMX-ONEGZZNKSA-N

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General description

Pterostilbene (trans-3,5-dimethoxy-4-hydroxystilbene), an antioxidant is an analogue of resveratrol. It is present in blueberries, tree wood and some types of grapes.

Application

Pterostilbene has been used:
  • to investigate its anti-oxidative stress activities and the involvement of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-antioxidant response element (ARE) signaling pathway
  • to determine its effects on transcriptional activation of estrogen receptor-α (ERα) in hormone resistant breast cancer cells)
  • to study its effects on the cytotoxicity of 2-chloroethyl ethyl sulphide (CEES) in human epidermoid carcinoma cells (A-431) through MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide)viability assay

Biochem/physiol Actions

Pterostilbene exhibits antineoplastic properties in some of the malignancies, hence it is considered as an active anticancer agent. It has the ability to stimulate apoptosis and block the viability of cell in estrogen-receptor positive and negative breast cancer cell lines.
Antioxidant, antiproliferative, apoptosis inducer, antihyperglycemic, antidiabetic.

Caution

Air-sensitive

Pictograms

CorrosionEnvironment
GHS05,GHS09

Signal Word

Danger

Hazard Statements

H318,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wasamon Nutakul et al.
Journal of agricultural and food chemistry, 59(20), 10964-10970 (2011-09-23)
The effects of resveratrol and pterostilbene (two structurally related stilbene compounds) on three human colon cancer cells were systematically compared. Cell viability tests indicated that IC(50) values of pterostilbene were 2-5-fold lower than those of resveratrol in all three cancer
Ebselen analogues reduce 2-chloroethyl ethyl sulphide toxicity in A-431 cells
Pino M A, et al.
Arhiv za Higijenu Rada i Toksikologiju, 64(1), 77-86 (2013)
Victor Chia-Hsiang Lin et al.
Journal of agricultural and food chemistry, 60(25), 6399-6407 (2012-06-08)
Prostate cancer is one of the leading causes of cancer death in men in Western countries. Epidemiological studies have linked the consumption of fruits and vegetables to a reduced risk of prostate cancer, and small fruits are particularly rich sources
A novel combinatorial epigenetic therapy using resveratrol and pterostilbene for restoring estrogen receptor-alpha (ER alpha) expression in ER alpha-negative breast cancer cells
Kala R and Tollefsbol T O
PLoS ONE, 11(5), e0155057-e0155057 (2016)
Keitaro Hagiwara et al.
Scientific reports, 2, 314-314 (2012-03-17)
It is well known that natural products are a rich source of compounds for applications in medicine, pharmacy, and biology. However, the exact molecular mechanisms of natural agents in human health have not been clearly defined. Here, we demonstrate for
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