ChemicalBook > CAS DataBase List > Ursonic acid

Ursonic acid

Product Name
Ursonic acid
CAS No.
6246-46-4
Chemical Name
Ursonic acid
Synonyms
3-Ketone;CCRIS 7123;TOS-BB-0966;Ursomic acid;URSONIC ACID;Arbutin acid;Ursonic acid, >98%;3-Ketoursolic acid;3-Oxours-12-en-28-oicaci;3-oxours-12-en-28-oic acid
CBNumber
CB0855178
Molecular Formula
C30H46O3
Formula Weight
454.68
MOL File
6246-46-4.mol
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Ursonic acid Property

Melting point:
284-285 °C
Boiling point:
555.1±50.0 °C(Predicted)
Density 
1.09±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO : 10 mg/mL (21.99 mM; Need ultrasonic and warming)
form 
powder to crystal
pka
4.68±0.70(Predicted)
color 
White to Almost white
InChIKey
MUCRYNWJQNHDJH-OADIDDRXSA-N
SMILES
C1(=O)[C@@]([C@]2([C@](C)(CC1)[C@]1([H])[C@@]([C@]3(C(=CC1)[C@]1([C@@](CC[C@H]([C@@H]1C)C)(C(O)=O)CC3)[H])C)(C)CC2)[H])(C)C
CAS DataBase Reference
6246-46-4
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Safety

HS Code 
2918.30.9000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

TCI Chemical
Product number
O0508
Product name
3-Oxours-12-en-28-oic Acid
Packaging
100MG
Price
$181
Updated
2024/03/01
Usbiological
Product number
299823
Product name
3-oxo-urs-12-en-28-oic acid
Packaging
10mg
Price
$546
Updated
2021/12/16
Matrix Scientific
Product number
098522
Product name
3-Oxours-12-en-28-oic acid
Purity
95+%
Packaging
1g
Price
$565
Updated
2021/12/16
AK Scientific
Product number
W2620
Product name
Ursonicacid
Packaging
1g
Price
$812
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
SHG0005740
Product name
3-OXOURS-12-EN-28-OIC ACID
Purity
95.00%
Packaging
1G
Price
$1575
Updated
2021/12/16
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Ursonic acid Chemical Properties,Usage,Production

Chemical Properties

Ursonic acid (UNA; 3-Oxo-urs-12-en-28-oic acid) is a polycyclic triterpenoid. As the polarity of UNA is also low, ethanol and methanol, which are less polar than water, can dissolve UNA. Ursolic acid (ULA) and UNA commonly belong to ursane-type triterpenoids, and their basic structures are characterized by five rings, a double bond between C-12 and C-13, and a carboxyl group at the C-28 position. Both ULA and UNA hold three oxygen atoms, which can activate ligands and donate lone electron pairs to transition metals. The carboxyl group at the C-28 position significantly enhances the pharmacological potency of triterpenoids. The structure of UNA is quite similar to that of ULA, with UNA possessing a keto group at the C-3 position instead of the β-hydroxy group found in ULA. This difference in the C-3 position may explain the dissimilar biological activities of the two compounds[1].

Occurrence

Ursonic acid (UNA) can be found in several parts of various plants used in traditional herbal medicines. According to previous studies, UNA can be extracted from Crataegus pinnatifida and Malus baccata fruits. In particular, UNA is one of the primary compounds present in the ripened fruits of Ziziphus jujuba. It was reported that resins from Pistacia atlantica, Bursera delpechiana, and trees of the Dipterocarpaceae family contain triterpenoids, including UNA. UNA is also found in the roots of Toona sinensis, Piper betle, and Ficus microcarpa. Extraction of aerial parts of Lantana camara, which was traditionally used for the treatment of eczema, ulcers, rheumatism, and malaria, also resulted in the isolation of UNA. It is known that UNA can be obtained from the leaves of Lantana tiliaefolia and Rauvolfia vomitoria. Furthermore, UNA was isolated from a whole Catharanthus Roseus and Dracocephalum komarovi plant, which are widely used as folk medicines in Asia, Europe, and Africa. This extensive presence of UNA in medicinal herbs suggests that UNA itself can exert therapeutic potential against diseases such as cancer and infectious protozoa[1].

References

[1] Juhyeon Son, Sang Yeol Lee. “Therapeutic Potential of Ursonic Acid: Comparison with Ursolic Acid.” Biomolecules (2020).

Uses

Ursonic acid (UNA) is a phytochemical which can be also extracted from a great variety of traditional medicinal herbs. It can be used as a cosmetics additive and serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents. Ursonic acid induces the apoptosis of human cancer cells through multiple signaling pathways.

Definition

ChEBI: Ursonic acid is a triterpenoid. It is a natural product found in Bursera linanoe, Lantana camara, and other organisms with data available.

Biological Activity

Ursonic acid is a natural triterpene acid that can induce apoptosis in human cancer cells through various signaling pathways.

Synthesis

3-oxo-12-en-28-ursolic acid (2) was obtained after compound 1 was refluxed in acetone under the action of Jones reagent for 5 hours, and then a series of anti-tumor Active novel quinoline oxadiazole derivatives.

target

Human Endogenous Metabolite

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Ursonic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Ursonic acid manufacturers

Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Product
3-Oxours-12-en-28-oic acid 6246-46-4
Price
US $0.00/g
Min. Order
1g
Purity
HPLC≥98%
Supply Ability
100kg
Release date
2024-03-14
Shanghai Standard Technology Co., Ltd.
Product
3-Oxours-12-en-28-oic acid 6246-46-4
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-08-13
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
3-oxo-urs-12-en-28-oic acid 6246-46-4 6246-46-4
Price
US $40.00/mg
Min. Order
20mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-07-18

6246-46-4, Ursonic acidRelated Search:


  • 3-oxours-12-en-28-oic acid
  • Ursonic acid, >98%
  • 3-oxo-urs-12-en-28-oic acid 6246-46-4
  • Ursomic acid
  • 3-Ketone
  • 3-Ketoursolic acid
  • CCRIS 7123
  • TOS-BB-0966
  • Urs-12-en-28-oic acid, 3-oxo-
  • 3-Oxours-12-en-28-oicaci
  • (1S,2R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
  • URSONIC ACID
  • Ursonic Acid,Endogenous Metabolite,Inhibitor,Apoptosis,inhibit
  • Arbutin acid
  • 6246-46-4
  • Pentacyclic Triterpenes