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Details

Stereochemistry RACEMIC
Molecular Formula C13H20O3
Molecular Weight 224.2961
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE, (4S,3R)-(E)-(±)-

SMILES

C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C

InChI

InChIKey=KPQMCAKZRXOZLB-KOIHBYQTSA-N
InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H20O3
Molecular Weight 224.2961
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including Nat. Prod. Lett. 1999, 14, 77−81 | http://www.tandfonline.com/doi/abs/10.1080/10575639908045437

4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, (4S,3R)-(E)-(±)- (Blumenol A) is a major secondary metabolite initially isolated from the leaves of Annona glabra L. (Annonaceae), commonly known as pond apple, which is a tropical tree distributed mainly in the Americas and in Southeast Asia, and used in traditional medicine as an insecticide and a parasiticide. Blumenol A was reported to display inhibitory activity against a panel of human solid tumor cell lines

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Metabolites from carnivorous fungus Arthrobotrys entomopaga and their functional roles in fungal predatory ability.
2013-05-01
[Vomifoliol: terpene alcohol isolated from leaves of Rauwolfia vomitoria Afz].
1969-03
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Vomifoliol was dissolved in 80% EtOH to a final concentration of 2 mg/mL. 5 μL of extract was impregnated into sterile Whatman No. 1 filter paper discs (6 mm diameter) and dried under a stream of sterile air. The bacterial pathogen N. gonorrhoeae (ATCC 49226 from ATCC as Kwik-STK™ plus microorganism) with viable counts reaching 10^8 CFU/mL was then streaked with sterile swabs onto Petri dishes containing chocolate (GC) agar base medium (CMO367, Oxoid Ltd., England) supplemented with 2% (w/v) hemoglobin and 1% (v/v) Vitox and the plates dried for 5 min at room temperature. The procedure was done in triplicate. Ciprofloxacin (1 μg/disc) was used as a positive control, while H2O and 80% EtOH were used as negative and solvent controls, respectively. Discs were applied to the dry surface of a Petri dish containing GC agar base medium and bacteria.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:19:54 GMT 2025
Edited
by admin
on Mon Mar 31 21:19:54 GMT 2025
Record UNII
B7QV234K84
Record Status Validated (UNII)
Record Version
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Name Type Language
FEMA NO. 4661, (4S,3R)-(E)-(±)-
Preferred Name English
4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE, (4S,3R)-(E)-(±)-
Systematic Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (R*,S*-(E))-
Common Name English
(±)-BLUMENOL-A
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (R*,S*-(E))-(±)-
Common Name English
(±)-VOLIFOLIOL
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-((1E,3R)-3-HYDROXY-1-BUTEN-1-YL)-3,5,5-TRIMETHYL-, (4S)-REL-
Common Name English
Code System Code Type Description
CAS
50763-73-0
Created by admin on Mon Mar 31 21:19:54 GMT 2025 , Edited by admin on Mon Mar 31 21:19:54 GMT 2025
PRIMARY
FDA UNII
B7QV234K84
Created by admin on Mon Mar 31 21:19:54 GMT 2025 , Edited by admin on Mon Mar 31 21:19:54 GMT 2025
PRIMARY