Skip to Content
MilliporeSigma

A9861

Auraptene

≥98% (HPLC)

Synonym(s):

7-Geranyloxycoumarin, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one, Aurapten

Slide 1 of 1
Sign In to View Organizational & Contract Pricing

Select a Size

5 MG

$109.65

25 MG

$389.00

$109.65

List Price$129.00Save 15%

Available to ship TODAYDetails

Request a Bulk Order

About This Item

Empirical Formula (Hill Notation):
C19H22O3
CAS Number:
495-02-3
Molecular Weight:
298.38
MDL number:
MFCD00075948
UNSPSC Code:
12352200
PubChem Substance ID:
329771062
NACRES:
NA.77

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\C(C)=C\COc1ccc2C=CC(=O)Oc2c1

InChI

1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

InChI key

RSDDHGSKLOSQFK-RVDMUPIBSA-N

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
E137954826SML3107
Auraptene ≥98% (HPLC)

Sigma-Aldrich

A9861

Auraptene

7-Ethoxycoumarin

Sigma-Aldrich

E1379

7-Ethoxycoumarin

Umbelliferone analytical standard

Supelco

54826

Umbelliferone

Glycycoumarin ≥98% (HPLC)

Sigma-Aldrich

SML3107

Glycycoumarin

assay

≥98% (HPLC)

assay

≥99.45% (HPLC)

assay

≥98.0% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

-

form

powder

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: >20 mg/mL

solubility

95% ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

-

solubility

DMSO: 2 mg/mL, clear

color

white to off-white

color

-

color

-

color

white to beige

General description

Auraptene (7-geranyloxycoumarin) is a prenyloxycoumarin, that is abundantly present in nature. It is produced by several plant species, such as Rutaceae and Umbeliferae (Apiaceae) families.[1]

Biochem/physiol Actions

Auraptene is an ACAT inhibitor and estrogen receptor modulator.
Auraptene is an estrogen receptor modulator that also acts as an ACAT inhibitor. It displays anti-tumor effects in several xenograft and chemically-induced murine tumor models. Auraptene induces apoptosis and is anti-proliferative in cancer cell lines. It has agonistic properties against PPARs, and interferes with lipid and cholesterol production by inhibiting ACAT (IC50 = 4 uM).
Auraptene (7-geranyloxycoumarin) possesses anti-oxidant, anti-bacterial, anti-inflammatory and anti-tumor activities.[2]

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000157986
0000067166
0000064559
072M4754V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Auraptene induces apoptosis via myeloid cell leukemia 1-mediated activation of caspases in PC3 and DU145 prostate cancer cells
Lee J C, et al.
Phytotherapy Research, 31(6), 891-898 (2017)
Auraptene and Its Role in Chronic Diseases
Drug Discovery from Mother Nature, 399-407 (2016)
Akira Murakami
Forum of nutrition, 61, 193-203 (2009-04-16)
A regulated low level of nitric oxide (NO) production in the body is essential for maintaining homeostasis (neuroprotection, vasorelaxation, etc.), though certain pathophysiological conditions associated with inflammation involve de novo synthesis of inducible NO synthase (iNOS) in immune cells, including
Salvatore Genovese et al.
Current drug targets, 12(3), 381-386 (2010-10-20)
Auraptene is the most abundant prenyloxycoumarin that occurs in nature. It has been isolated from plants belonging to many genus of the Rutaceae family, comprising several edible fruits and vegetables. Although known for a long time, only in the last
Hirotaka Sekiguchi et al.
Bioscience, biotechnology, and biochemistry, 74(5), 1018-1024 (2010-05-13)
Helicobacter pylori (H. pylori) is a major human pathogen and plays a central role in chronic gastritis and gastric cancer. Since the adhesion of H. pylori to the human gastric epithelium is the initial and critical step of its infection
View All Related Papers

Articles

Nuclear Receptors (Steroids)

We offers many products related to Nuclear Receptors (Steroids) for your research needs.

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service