Ursolic acid

Iupac Name：(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

CAS No.: 77-52-1

Molecular Weight：456.70032

Modify Date.: 2022-11-29 02:58

Introduction: A Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties. View more+

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1. Names and Identifiers

1.1 Name: Ursolic acid
1.2 Synonyms: (+)-Ursolic acid (1S,2R,4aS,6aS,6aS,6bR,8aS,10S,12aS,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid (1S,2R,4aS,6aS,6bR,10S,12aS,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid (3beta)-3-Hydroxyurs-12-en-28-oic acid (3β)-3-Hydroxyurs-12-en-28-oic acid 10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid 3beta-Hydroxyurs-12-en-28-oic acid 3β-Hydroxyurs-12-en-28-oic acid Bungeolic acid Malol Merotaine Neoage UR NSC 167406 NSC 4060 Prestwick_355 Prunol Urs-12-en-28-oic acid, 3.beta.-hydroxy- Urs-12-en-28-oic acid, 3beta-hydroxy- (8CI) Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)- Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)- Urs-12-en-28-oic acid, 3-hydroxy-, (3β)- Urs-12-en-28-oic acid, 3β-hydroxy- Ursolic Acid Ursolicacid Ursoliic acid Ursolisome Urson β-Ursolic acid

1.3 CAS No.: 77-52-1

1.4 CID: 64945

1.5 EINECS(EC#): 201-034-0

1.6 Molecular Formula: C30H48O3 (isomer)

1.7 Inchi: InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

1.8 InChkey: WCGUUGGRBIKTOS-GPOJBZKASA-N

1.9 Canonical Smiles: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O

1.10 Isomers Smiles: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O

2. Properties

2.1 Density: 1.09

2.1 Melting point: 283-285℃

2.1 Boiling point: 556.9°C at 760 mmHg

2.1 Refractive index: 1.4940 (estimate)

2.1 Flash Point: 304.6°C

2.1 Precise Quality: 456.36000

2.1 PSA: 57.53000

2.1 logP: 7.08950

2.1 Appearance: Solid

2.2 Chemical Properties: white to light yellow crystal powde

2.3 Color/Form: Powder

2.4 pKa: 4.68±0.70(Predicted)

2.5 Water Solubility: H2O: insoluble

2.6 Spectral Properties: Specific optical rotation: +67.5 deg at 21 deg C/D ( c = 1 in N alcohol KOH)

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.

3.2 Usage: A Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 Octanol/Water Partition Coefficient: log Kow = 7.92 (est)

4.2 Hazard Declaration: H413

4.2 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.3 RIDADR: OTH

4.3 WGK Germany: -

4.3 RTECS: YU9520000

4.3 Safety: Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:24/25-36-26
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:-

4.4 Specification: white to light yellow crystal powde
usageEng:A Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.
Safety Statements:24/25-36-26
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

77-52-1Total: 6 Synthesis Route

915-32-2

77-52-1 466 Suppliers

Literatures:
Sengupta, Pasupati; Sen, Manju; Das, Saktipada Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980 , vol. 19, # 8 p. 721 - 722
Yield: ~71%

127-09-3 740 Suppliers

77-52-1 466 Suppliers

508-02-1 288 Suppliers

Literatures:
Journal of the Chemical Society, Chemical Communications, , # 14 p. 1141 - 1143
Yield: null

28288-99-5

50-99-7 475 Suppliers

77-52-1 466 Suppliers

Literatures:
Egyptian Journal of Chemistry, , vol. 54, # 1 p. 99 - 113
Yield: null

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7. Precursor and Product

precursor:

915-32-2

28288-99-5

1381876-19-2

104668-95-3

127-09-3

1198208-27-3

product :

1724-17-0

2131-43-3

915-32-2

192211-41-9

856012-03-8

869788-71-6

4547-24-4

545-46-0

582-16-1

488-23-3

486-34-0

508-02-1

8. Other Information

8.0 Origins: Ursolic acid can be isolated from various medicinal plants, Lamiaceae family being one of the most known sources of triterpenes, with contents up to 2.95% d.w^[8]. In Rosmarinus officinalis leaves, one of the traditional commercial sources^[9]. UA has also been identified in a variety of sources, particularly in leaves and flowers^[10]. The triterpenic acids oleanolic and ursolic were recently detected for the first time in wild edible mushrooms^[11] and in some commercial dried fruits^[12].
UA content in the samples from different sources were significantly different, and the geographic variation was also observed in Paulownia fortune, Ocimum species, Argania spinosa^[13]. The outer barks of Eucalyptus trees from temperate and Mediterranean zones are richer in triterpenic acids than the species from sub-tropical and tropical regions^[14].

8.1 Properties and biological effects: Ursolic acid displayed lower toxicity than OA, 0.95 up from 0.10 mg/mL, respectively^[15], but the data ranged depending on the raw material source, the extraction solvent, the type of activity, the disease, the clinical, cosmetically or pharmacological study, the study in animal or human, etc. Bioavailability studies confirmed a low plasma concentrations of UA in plasma of mice orally administered with high dose of UA, suggested either high binding activity in organs or low bioavailability or metabolism by the gut wall of the intestine and liver^[16]. Despite many aspects of the biological activities of UA are not completely understood, the pharmacological effects could be attributed, in part, to their action against free radicals. Cardiovascular protection and anti-hyperlipidemic effect Cardiovascular protection, antihyperlipidemic (triglycerides, total cholesterol and lipoprotein fractions), antioxidant (glutathione peroxidase and superoxide dismutase activities), hypoglycemic effects and prevention of hypertension were observed in rats, displaying UA a low toxicity (LC50 0.95 mg/mL). Ursolic acid fed to rabbits and rats prevented the experimental atherosclerosis and lowered blood cholesterol^[17]. A strong synergistic effect derived from the combination of ursolic acid and artesunate can reduce both triglyceride and cholesterol, showing more potent effects than either agent alone. Ethanolic extract from the stems and roots of Celastrus orbiculatus Thunb decreases athero-susceptibility in lipoproteins and the aorta of guinea pigs fed a high-fat diet, and increases high-density lipoprotein; likewise, it reduce lipid accumulation and promote reverse cholesterol transport in vivo and in vitro^[18].
Antitumor effect
Beneficial action of ursolic acid and its derivatives was reported based on their anti-tumor, including inhibition of angiogenesis, invasion of tumor cells and metastasis, induction of apoptosis in tumor cells and prevention of malignant transformation of normal cells, and it also interferes with numerous enzymes^[19]. Clinical tests suggesting the possibility of practical use of UA have already been conducted^[20]. Ursolic acid was identified as active components of different plants for inhibiting mutagenicity and tumor-promotion. Ursolic acid exert anticancer effects in various cancer cell systems^[20], it may have a potential application as a chemopreventive agent in gastric cancer, colorectal carcinogenesis and tumors of the colon, lung cancer, prostate cancer, UA pretreatment potentiated cell cycle arrest and UV radiation-induced apoptosis selectively in skin melanoma cells^[21].
Antimicrobial
Ursolic acid and its derivatives have shown growth inhibition of gram-positive and gram-negative bacteria and fungi, and UA showed ability to control bacterial growth, biofilm formation, and elastase activity^[22]. Synergistic effect of UA and two semi-synthetic derivatives and the aminoglycosides antibiotics neomycin, amikacin, kanamycin and gentamicin towards twelve bacterial pathogens strains was observed. Ursolic acid is the active components in natural extracts to inhibit the growth of some food-associated bacteria and yeast, protozoa (Trypanosoma cruzi), promoting an anti-inflammatory response during Leishmania infection^[23].
Anti-diabetes, anti-inflammatory and anti-aging effect
Ursolic acid exhibits potential anti-diabetic and immunomodulatory properties by increasing insulin levels with preservation of pancreatic beta-cells and modulating blood glucose levels, T-cell proliferation and cytokines production by lymphocytes in type 1 diabetic mice fed a high-fat diet, compared to the diabetic group^[24]. Type-2 diabetes is associated with obesity and ursolic acid may prevent or treat this disorder and its related comorbidities by acting as hypoglycemic and anti-obesity agent with five effects: reduction of the absorption of glucose, decrease the endogenous glucose production and increase the glycogen synthesis, increase the insulin sensitivity, improvement of lipid homeostasis, and promotion of the body weight regulation^[9].
UA was twice as potent as indomethacin, and has been proposed for the treatment of rheumatism, fever and arthritis. The mechanisms of the anti-inflammatory action of ursolic acid and novel derivatives may be ascribed to inhibition of histamine release from mast cells, lipoxygenases, cyclooxygenases activity, inducible nitric oxide synthase and elastase, suppress the inflammatory cytokine-induced expression of E-selectin (an early response adhesion molecule expressed on the surface of endothelial cells during inflammation) in endothelial cells via inhibition of NF-kappa B activation^[25] and suppressed the production of intracellular reactive oxygen species^[26].
The epidermal permeability barrier plays a crucial role in human physical, chemical and biological cutaneous functions. Sensitive skin, associated with increased transepidermal water loss, penetrability and susceptibility to irritants, is related with impaired barrier function and reduction in ceramides. The atopic dermatitis displays impaired epidermal permeability barrier function, diminished water-holding properties and decreased ceramide levels. UA are great moisturizing candidates that do not create any cutaneous irritations^[27]. Induction of ceramide synthesis is usually associated with keratinocyte differentiation. The ursolic acid increases the expression of genes required for terminal keratinocyte differentiation (involucrin, loricrin and filaggrin), improving the recovery of skin barrier function.

8.2 Chemical Properties: white to light yellow crystal powde

8.3 Uses: A Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.

8.4 Uses: ursolic acid helps maintain the look and feel of the skin, acts as a perfume and helps mask odor. Therapeutic benefits in skin care include anti-inflammatory activity. ursolic acid has demonstrated anti-microbial, anti-bacterial, and anti-fungal action as well.

8.5 Definition: ChEBI: A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.

8.6 Manufacturing Info: Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-: ACTIVE

8.7 Merck: 14,9890

8.8 BRN: 2228563

9. Computational chemical data

Molecular Weight: 456.70032g/mol
Molecular Formula: C₃₀H₄₈O₃
Compound Is Canonicalized: True
XLogP3-AA: 7.3
Exact Mass: 456.36034539
Monoisotopic Mass: 456.36034539
Complexity: 874
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 57.5
Heavy Atom Count: 33
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGCAAAAAADAAAAAGgAACAAADxSggAICCAAAAgCIAiDSCAAAAAAgAAAACAEAAAgAEBIAAQAAQAAEgAAIAAOIyPCPgAAAAAAAAADAAAYAADAAAAAAAAAAAA==

10. Question & Answer

What is Ursolic Acid? Feb 11 2022
Benefits Of Ursolic Acid Build muscle Ursolic acid can increase muscle strength and reduce a laboratory marker of muscle damage. Lose weight Ursolic acid may help reduce body weight, BMI and waist circumference. Diabetes Ursolic acid can improve fasting blood glucose levels and insulin sensitivity....

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12. Realated Product Infomation

7372-30-7 Ursolic acid acetate

32208-45-0 URSOLIC ACID METHYL ESTER

192211-41-9 Benzyl ursolate

220435-39-2 SODIUM URSOLATE

19132-81-1 Ursolic aldehyde

71010-76-9 Decanoic acid, mixed esters with heptanoic acid, octanoic acid, pentaerythritol and valeric acid

68130-55-2 Hexanedioic acid, mixed esters with decanoic acid, heptanoic acid, octanoic acid and pentaerythritol

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