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H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Sinônimo(s):

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

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5 MG
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5 MG
R$ 2.075,00

About This Item

Fórmula empírica (Notação de Hill):
C26H33NO2
Número CAS:
Peso molecular:
391.55
Número MDL:
Código UNSPSC:
12352106
ID de substância PubChem:
NACRES:
NA.77

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fonte biológica

synthetic (organic)

Ensaio

≥95%

Formulário

powder

cor

yellow to yellow-orange

temperatura de armazenamento

−20°C

cadeia de caracteres 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+

chave InChI

AKJHMTWEGVYYSE-FXILSDISSA-N

Descrição geral

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.[1]

Aplicação

Retinoic acid p-hydroxyanilide has been used:
  • as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes[1]
  • as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation[2]
  • to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)[3]

Ações bioquímicas/fisiológicas

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis.[1] It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis.[2] Fenretinide may elicit anticancer activity in cultured human breast cancer cells.[2] It acts as an insulin antagonist and may be useful in treating insulin resistance.[2] Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.[3]
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

Pictogramas

Health hazardExclamation mark

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


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Dušan Garić et al.
Journal of molecular medicine (Berlin, Germany), 95(10), 1053-1064 (2017-07-12)
Cystic fibrosis is the most common genetic disease, in which symptoms may be alleviated but not fully eliminated. Ceramides have long been implicated in the inflammatory etiology of cystic fibrosis, with contradicting reports with regards to their role. Recently, significant
Adriana Albini et al.
Nature reviews. Clinical oncology, 9(9), 498-509 (2012-08-02)
Healthy individuals can harbour microscopic tumours and dysplastic foci in different organs in an undetectable and asymptomatic state for many years. These lesions do not progress in the absence of angiogenesis or inflammation. Targeting both processes before clinical manifestation can
Michael M Song et al.
Anti-cancer drugs, 30(2), 117-127 (2018-10-03)
All-trans-N-(4-hydroxyphenyl)retinamide or fenretinide (4-HPR) acts by reactive oxygen species (ROS) and dihydroceramides (DHCers). In early-phase clinical trials 4-HPR has achieved complete responses in T-cell lymphomas (TCL) and neuroblastoma (NB) and signals of activity in ovarian cancer (OV). We defined the
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
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

Artigos

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.

Questions

1–3 of 3 Questions  
  1. In what solvents can product H7779, Retinoic acid p-hydroxyanilide, be dissolved?

    1 answer
    1. Product H7779, Retinoic acid p-hydroxyanilide, can be dissolved in DMSO (25 mg/ml) and ethanol (25 mg/ml).

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  2. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  3. How can one store a solution of product H7779, Retinoic acid p-hydroxyanilide?

    1 answer
    1. A solution of product H7779, Retinoic acid p-hydroxyanilide, can be aliquoted and stored at -20°C for up to 3 months. Solutions should be protect from light.

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