Betulinaldehyde

Modify Date: 2025-08-25 20:30:13

Betulinaldehyde Structure
Betulinaldehyde structure
 Common Name Betulinaldehyde
CAS Number 13159-28-9 Molecular Weight 440.701
Density 1.0±0.1 g/cm3 Boiling Point 513.9±33.0 °C at 760 mmHg
Molecular Formula C30H48O2 Melting Point N/A
MSDS N/A Flash Point 217.4±18.0 °C

 Use of Betulinaldehyde


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].

 Names

Name Betulinicaldehyde
Synonym More Synonyms

 Betulinaldehyde Biological Activity

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].
Related Catalog
References

[1]. Chung PY, et al. Identification, by gene expression profiling analysis, of novel gene targets in Staphylococcus aureus treated with betulinaldehyde. Res Microbiol. 2013 May;164(4):319-26.

[2]. Chung PY, et al. Transcriptional profiles of the response of methicillin-resistant Staphylococcus aureus to pentacyclic triterpenoids. PLoS One. 2013;8(2):e56687.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 513.9±33.0 °C at 760 mmHg
Molecular Formula C30H48O2
Molecular Weight 440.701
Flash Point 217.4±18.0 °C
Exact Mass 440.365417
PSA 37.30000
LogP 9.07
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.545
InChIKey FELCJAPFJOPHSD-ROUWMTJPSA-N
SMILES C=C(C)C1CCC2(C=O)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12
Storage condition -20°C

 Synthetic Route

Betulin structure

Betulin

CAS#:473-98-3

~17%

3,28-Dioxolup-22,29-en structure

3,28-Dioxolup-2...

CAS#:4439-98-9

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: Bioorganic and Medicinal Chemistry, , vol. 10, # 10 p. 3229 - 3236
Betulin structure

Betulin

CAS#:473-98-3

~91%

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: Csuk, Rene; Schmuck, Kianga; Schaefer, Renate Tetrahedron Letters, 2006 , vol. 47, # 49 p. 8769 - 8770
Betulin structure

Betulin

CAS#:473-98-3

~%

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Betulinic acid structure

Betulinic acid

CAS#:472-15-1

Literature: STORA ENSO OYJ; WICKHOLM, Niko; ALAKURTTI, Sami; YLI-KAUHALUOMA, Jari; KOSKIMIES, Salme Patent: WO2013/38316 A1, 2013 ; Location in patent: Page/Page column 15 ;
Betulinic acid structure

Betulinic acid

CAS#:472-15-1

~4%

Betulin structure

Betulin

CAS#:473-98-3

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: Phytochemistry (Elsevier), , vol. 36, # 6 p. 1369 - 1380
(3β)-N-methyl-N-methoxy-3-acetoxylup-20(29)-en-28-amide structure

(3β)-N-methyl-N...

CAS#:1025068-55-6

~%

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: WO2008/57420 A2, ; Page/Page column 280-281 ;
O,O'-bis-(trimethylsilyl)-betulin structure

O,O'-bis-(trime...

CAS#:212708-99-1

~%

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: Barthel, Alexander; Stark, Sebastian; Csuk, Rene Tetrahedron, 2008 , vol. 64, # 39 p. 9225 - 9229
Betulin structure

Betulin

CAS#:473-98-3

~7%

3,28-Dioxolup-22,29-en structure

3,28-Dioxolup-2...

CAS#:4439-98-9

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Betulinic acid structure

Betulinic acid

CAS#:472-15-1

Detail
Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 8, # 13 p. 1707 - 1712
Betulin structure

Betulin

CAS#:473-98-3

~35%

3,28-Dioxolup-22,29-en structure

3,28-Dioxolup-2...

CAS#:4439-98-9

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

3-Oxobetulin structure

3-Oxobetulin

CAS#:7020-34-0

Literature: Chemistry of Natural Compounds, , vol. 38, # 1 p. 58 - 61
3-O-acetylbetulinaldehyde structure

3-O-acetylbetul...

CAS#:27570-21-4

~%

Betulinaldehyde Structure

Betulinaldehyde

CAS#:13159-28-9

Literature: Helvetica Chimica Acta, , vol. 24, p. 529 Helvetica Chimica Acta, , vol. 25, p. 171 Chemische Berichte, , vol. 65, p. 1305

 BetulinaldehydeBioassay

View more

Name: Growth inhibition of mouse B16 2F2 cells after 3 days
Source: ChEMBL
Target: B16
External Id: CHEMBL961866
Name: Induction of apoptosis in mouse B16 2F2 cells assessed as condensation and fragmentat...
Source: ChEMBL
Target: B16
External Id: CHEMBL961868
Name: Antimycobacterial activity against Mycobacterium tuberculosis H37Rv after 7 days by m...
Source: ChEMBL
Target: Mycobacterium tuberculosis
External Id: CHEMBL4252990
Name: HIV Enzyme Data
Source: NIAID
Target: N/A
External Id: HIV Enzyme Data
Name: Inhibition of Saccharomyces sp. alpha-glucosidase
Source: ChEMBL
Target: N/A
External Id: CHEMBL983400
Name: Antiproliferative activity against mouse +SA mammary epithelial cells after 4 days by...
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL1024779
Name: Inhibition of human CD73 assessed as reduction in inorganic phosphate release upon su...
Source: ChEMBL
Target: 5'-nucleotidase
External Id: CHEMBL5146032
Name: Cytotoxicity against human HuH7 cells assessed as cell viability at 50 uM after 24 hr...
Source: ChEMBL
Target: N/A
External Id: CHEMBL1099856
Name: Antiviral activity against SFV infected in BHK cells assessed as surviving virus frac...
Source: ChEMBL
Target: Semliki Forest virus
External Id: CHEMBL1099853
Name: Toxicity against peritoneal macrophages assessed as survival induces at 68 uM
Source: ChEMBL
Target: N/A
External Id: CHEMBL1071064
Total 13, Current Page 1 of 2
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 Synonyms

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

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