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Betulinicaldehyde

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-B2004

  • Specification : 98%

  • CAS number : 13159-28-9

  • Formula : C30H48O2

  • Molecular Weight : 440.7

  • PUBCHEM ID : 99615

  • Volume : 20mg

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Catalogue Number

BF-B2004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

440.7

Appearance

White crystalline powder

Botanical Source

leaves of Dillenia turbinata Finetet Gagnep

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C=O

Synonyms

Lup-20(29)-en-28-al, 3β-hydroxy-/Lup-20(29)-en-28-al, 3-hydroxy-, (3β)-/(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde/(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carbaldehyde/(3β)-3-Hydroxylup-20(29)-en-28-al/Betulinaldehyde

IUPAC Name

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde

Density

1.0±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

217.4±18.0 °C

Boiling Point

513.9±33.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

FELCJAPFJOPHSD-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:13159-28-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30893801

Abstract

A series of 3-substituted derivatives of betulin and betulinic aldehyde were synthesized as promising anticancer agents. The newly triterpenes were tested against five human cancer cell lines like biphenotypic B myelomonocytic leukaemia (MV-4-11), adenocarcinoma (A549), prostate (Du-145), melanoma (Hs294T), breast adenocarcinoma (MCF-7) and normal human mammary gland (MCF-10A). The compound 9 showed towards Du-145, MCF-7 and Hs294T cells significant antiproliferative activity with IC50 ranging from 7.3 to 10.6 μM. The evaluation of ADME properties of all compounds also includes their pharmacokinetic profile. The calculated TPSA values for synthetized derivatives are in the range between 43.38 a² and 55.77 a² suggesting high oral bioavailability. The molecular docking calculations showed that triterpene 9 fits the active site of the serine/threonine protein kinase Akt.

KEYWORDS

ADME; antiproliferative activity; betulin; betulinic aldehyde; molecular docking

Title

Biological Activity and In Silico Study of 3-Modified Derivatives of Betulin and Betulinic Aldehyde.

Author

Bębenek E1, Chrobak E2, Marciniec K3, Kadela-Tomanek M4, Trynda J5, Wietrzyk J6, Boryczka S7.

Publish date

2019 Mar 19

PMID

30893801

Abstract

A series of 3-substituted derivatives of betulin and betulinic aldehyde were synthesized as promising anticancer agents. The newly triterpenes were tested against five human cancer cell lines like biphenotypic B myelomonocytic leukaemia (MV-4-11), adenocarcinoma (A549), prostate (Du-145), melanoma (Hs294T), breast adenocarcinoma (MCF-7) and normal human mammary gland (MCF-10A). The compound 9 showed towards Du-145, MCF-7 and Hs294T cells significant antiproliferative activity with IC50 ranging from 7.3 to 10.6 μM. The evaluation of ADME properties of all compounds also includes their pharmacokinetic profile. The calculated TPSA values for synthetized derivatives are in the range between 43.38 a2 and 55.77 a2 suggesting high oral bioavailability. The molecular docking calculations showed that triterpene 9 fits the active site of the serine/threonine protein kinase Akt.

KEYWORDS

betulin, betulinic aldehyde, antiproliferative activity, ADME, molecular docking

Title

Biological Activity and In Silico Study of 3-Modified Derivatives of Betulin and Betulinic Aldehyde

Author

Ewa Bębenek,1,* Elwira Chrobak,1 Krzysztof Marciniec,1 Monika Kadela-Tomanek,1 Justyna Trynda,2 Joanna Wietrzyk,3 and Stanisław Boryczka1

Publish date

2019 Mar 19


Description :

Betulinaldehyde(Betunal) belongs to pentacyclic triterpenoids and was reported to exhibit antimicrobial activities against bacteria and fungi, including S. aureus.IC50 value:Target: Betulinaldehyde(Betunal) belongs to pentacyclic triterpenoids that are based on a 30-carbon skeleton comprising four six-membered rings and one five-membered ring. Betulinaldehyde regulates multiple desirable targets which could be further explored in the development of therapeutic agents for the treatment of S. aureus infections [1]. Study compounds α-amyrin [3β-hydroxy-urs-12-en-3-ol (AM)], betulinic acid [3β-hydroxy-20(29)-lupaene-28-oic acid (BA)] and betulinaldehyde [3β-hydroxy-20(29)-lupen-28-al (BE)] belong to pentacyclic triterpenoids and were reported to exhibit antimicrobial activities against bacteria and fungi, including S. aureus. The MIC values of these compounds against a reference strain of methicillin-resistant S. aureus (MRSA) (ATCC 43300) ranged from 64 μg/ml to 512 μg/ml. However, the response mechanisms of S. aureus to these compounds are still poorly understood [2].