Accéder au contenu
MilliporeSigma
Toutes les photos(1)

Key Documents

Autres documents

H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Synonyme(s) :

4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule empirique (notation de Hill):
C26H33NO2
Numéro CAS:
65646-68-6
Poids moléculaire :
391.55
Numéro MDL:
MFCD00792674
Code UNSPSC :
12352106
ID de substance PubChem :
24278472
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥95%

Forme

powder

Couleur

yellow to yellow-orange

Température de stockage

−20°C

Chaîne SMILES 

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1

InChI

1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

Clé InChI

AKJHMTWEGVYYSE-FXILSDISSA-N

Description générale

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

Application

Retinoic acid p-hydroxyanilide has been used:
  • as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes
  • as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation
  • to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)

Actions biochimiques/physiologiques

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis. It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis. Fenretinide may elicit anticancer activity in cultured human breast cancer cells. It acts as an insulin antagonist and may be useful in treating insulin resistance. Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Les clients ont également consulté

Slide 1 of 2

1 of 2

Rétinol synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

Sigma-Aldrich

R7632

Rétinol

Cytosine β-D-arabinofuranoside crystalline, ≥90% (HPLC)

Sigma-Aldrich

C1768

Cytosine β-D-arabinofuranoside

Matthew J Watt et al.
Endocrine reviews, 40(5), 1367-1393 (2019-05-18)
The liver is a dynamic organ that plays critical roles in many physiological processes, including the regulation of systemic glucose and lipid metabolism. Dysfunctional hepatic lipid metabolism is a cause of nonalcoholic fatty liver disease (NAFLD), the most common chronic
C Marth et al.
Journal of the National Cancer Institute, 75(5), 871-875 (1985-11-01)
The synthetic retinoid 4-hydroxyphenylretinamide (HPR) showed antiproliferative effect on cultured human breast cancer cells, which were sensitive to retinoic acid (RA) too. Investigation of the cell cycle by flow cytophotometry showed a significant increase of cells in the S-phase of
D Delia et al.
Cancer research, 53(24), 6036-6041 (1993-12-15)
N-(4-Hydroxyphenyl)retinamide (HPR) is a synthetic retinoid of particular clinical interest in cancer chemoprevention. We have examined the in vitro effects of HPR on lymphoid and myeloid malignant cell lines and found that at concentrations between 10(-5) and 3 x 10(-7)
Claude Lachance et al.
Infection and immunity, 82(5), 1778-1785 (2014-02-20)
Streptococcus suis is an important swine pathogen and an emergent zoonotic pathogen. Excessive inflammation caused by S. suis is responsible for early high mortality in septic shock-like syndrome cases. Polyunsaturated fatty acids (PUFAs) may contribute to regulating inflammatory processes. This
Chunxiao Wang et al.
Biochemical and biophysical research communications, 493(4), 1555-1559 (2017-10-11)
In the absence of approved therapeutics, Zika virus (ZIKV)'s recent prolific outbreaks in the Americas, together with impacts on unborn fetuses of infected mothers, make it a pressing human health concern worldwide. Although a key player in viral replication in
Afficher tous les articles scientifiques apparentés

Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique