Drupanin

Modify Date: 2024-01-04 19:45:57

Drupanin Structure
Drupanin structure
 Common Name Drupanin
CAS Number 53755-58-1 Molecular Weight 232.27500
Density 1.165g/cm3 Boiling Point 393.3ºC at 760 mmHg
Molecular Formula C14H16O3 Melting Point N/A
MSDS N/A Flash Point 205.8ºC

 Use of Drupanin


Drupanin is a compound isolated from green propolis. Drupanin can selectively inhibit the AKR1C3 enzyme. Drupanin has the potential for the research of breast cancer[1].

 Names

Name (E)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
Synonym More Synonyms

 Drupanin Biological Activity

Description Drupanin is a compound isolated from green propolis. Drupanin can selectively inhibit the AKR1C3 enzyme. Drupanin has the potential for the research of breast cancer[1].
Related Catalog
References

[1]. Rodrigues DM, et al. Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis. Bioorg Med Chem. 2021;47:116372.

 Chemical & Physical Properties

Density 1.165g/cm3
Boiling Point 393.3ºC at 760 mmHg
Molecular Formula C14H16O3
Molecular Weight 232.27500
Flash Point 205.8ºC
Exact Mass 232.11000
PSA 57.53000
LogP 2.99870
Index of Refraction 1.608

 Synthetic Route

plicatin B structure

plicatin B

CAS#:72704-01-9

~87%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Menon, Sanjay R.; Patel, Vishal K.; Mitscher, Lester A.; Shih, Peter; Pillai, Segaran P.; Shankel, Delbert M. Journal of Natural Products, 1999 , vol. 62, # 1 p. 102 - 106
tert-butyl (E)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]acrylate structure

tert-butyl (E)-...

CAS#:1208233-14-0

~60%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Tani, Hiroko; Hasumi, Keiko; Tatefuji, Tomoki; Hashimoto, Ken; Koshino, Hiroyuki; Takahashi, Shunya Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 1 p. 151 - 157
methyl (E)-3-[4-(acetyloxy)-3-(3-methyl-2-butenyl)phenyl]-2-propenoate structure

methyl (E)-3-[4...

CAS#:151071-02-2

~82%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Bates, Roderick W.; Gabel, Christine J.; Ji, Jianhua; Rama-Devi, Thota Tetrahedron, 1995 , vol. 51, # 30 p. 8199 - 8212
4-Iodophenol structure

4-Iodophenol

CAS#:540-38-5

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Uto, Yoshihiro; Ae, Shutaro; Koyama, Daisuke; Sakakibara, Mitsutoshi; Otomo, Naoki; Otsuki, Mamoru; Nagasawa, Hideko; Kirk, Kenneth L.; Hori, Hitoshi Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 16 p. 5721 - 5728
4-IODO-2-(3-METHYL-2-BUTENYL)-PHENOL structure

4-IODO-2-(3-MET...

CAS#:151071-03-3

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Uto, Yoshihiro; Ae, Shutaro; Koyama, Daisuke; Sakakibara, Mitsutoshi; Otomo, Naoki; Otsuki, Mamoru; Nagasawa, Hideko; Kirk, Kenneth L.; Hori, Hitoshi Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 16 p. 5721 - 5728
Phenol, 4-iodo-2-(3-methyl-2-buten-1-yl)-, 1-acetate structure

Phenol, 4-iodo-...

CAS#:151071-04-4

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Uto, Yoshihiro; Ae, Shutaro; Koyama, Daisuke; Sakakibara, Mitsutoshi; Otomo, Naoki; Otsuki, Mamoru; Nagasawa, Hideko; Kirk, Kenneth L.; Hori, Hitoshi Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 16 p. 5721 - 5728
3,3-Dimethylallyl bromide structure

3,3-Dimethylall...

CAS#:870-63-3

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Uto, Yoshihiro; Ae, Shutaro; Koyama, Daisuke; Sakakibara, Mitsutoshi; Otomo, Naoki; Otsuki, Mamoru; Nagasawa, Hideko; Kirk, Kenneth L.; Hori, Hitoshi Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 16 p. 5721 - 5728
p-Hydroxy-cinnamic acid structure

p-Hydroxy-cinna...

CAS#:7400-08-0

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Menon, Sanjay R.; Patel, Vishal K.; Mitscher, Lester A.; Shih, Peter; Pillai, Segaran P.; Shankel, Delbert M. Journal of Natural Products, 1999 , vol. 62, # 1 p. 102 - 106
Methyl p-coumarate structure

Methyl p-coumarate

CAS#:3943-97-3

~%

Drupanin Structure

Drupanin

CAS#:53755-58-1

Literature: Menon, Sanjay R.; Patel, Vishal K.; Mitscher, Lester A.; Shih, Peter; Pillai, Segaran P.; Shankel, Delbert M. Journal of Natural Products, 1999 , vol. 62, # 1 p. 102 - 106

 Synonyms

(E)-3-[4-hydroxy-3-(3-methylbutenyl)phenyl]-2-propenoic acid
(E)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]acrylic acid
4-hydroxy-3-prenylcinnamic acid
3-prenyl-4-hydroxycinnamic acid
(E)-3-(4-Hydroxy-3-(3-methyl-2-butenyl)phenyl)-2-propenoic acid
2-Propenoic acid,3-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-,(2E)
(E)-3-prenyl-p-coumaric acid
drupanin
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