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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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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
Wei Wen et al.
Scientific reports, 7(1), 12754-12754 (2017-10-08)
Endometrial cancer is the most common gynecologic cancer in the United States and its incidence and mortality has been rising over the past decade. Few treatment options are available for patients with advanced and recurring endometrial cancers. Novel therapies, which
Rei Wakimoto et al.
Anticancer research, 37(11), 6153-6159 (2017-10-25)
Although pterostilbene, a natural analog of resveratrol, has potent antitumor activity against several human cancer types, the possible inhibitory mechanisms against subtypes of human breast cancer with different hormone receptor and human epidermal growth factor receptor 2 (HER2) status remain
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
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