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Ursolic acid
Cas No: 77-52-1
No Data 1 Gram 1 Metric Ton/Day Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Factory supply Loquat Leaf Extract Ursolic Acid 25% CAS 77-52-1
Cas No: 77-52-1
USD $ 25.32-25.32 / Kilogram 1 Kilogram 15 Metric Ton/Month Guang'an Hongyi Bio-technology Co., Ltd Contact Supplier
ursolic acid
Cas No: 77-52-1
USD $ 1.0-1.0 / Kilogram 1 Kilogram 25 Kilogram/Day ZHEJIANG PAULA INDUSTRY CO.,LTD Contact Supplier
High quality Ursolic acid manufacture 77-52-1
Cas No: 77-52-1
USD $ 80.0-100.0 / Kilogram 1 Kilogram 5000 Kilogram/Month Kono Chem Co.,Ltd Contact Supplier
Top Quality Raw Material 100% Pure Natural Herb Rosemary Extract 50% Ursolic Acid Powder
Cas No: 77-52-1
USD $ 74.0-84.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Xi'an Quanao Biotech Co., Ltd. Contact Supplier
High Purity Cosmetic Raw Materials Ursolic Acid Cas 77-52-1
Cas No: 77-52-1
USD $ 1000.0-1000.0 / Kilogram 1 Kilogram 5000 Kilogram/Month Metric Ton/Day Hebei Guanlang Biotechnology Co., Ltd. Contact Supplier
Ursolic acid 98% 95% 80% 50% 30% 25% 15% CAS: 77-52-1
Cas No: 77-52-1
No Data 1 Kilogram 2 Metric Ton/Month Elementary Chemical Co., Limited Contact Supplier
Arbutin
Cas No: 77-52-1
USD $ 18.0-18.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Greenutra Resource Inc Contact Supplier
High purity Ursolic acid with high quality and lowest pricre cas:77-52-1
Cas No: 77-52-1
USD $ 1105.0-1950.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
20% 25% 50% 98% up Ursolic acid Loquat Leaf Extract 77-52-1
Cas No: 77-52-1
No Data 1 Kilogram 1000 Kilogram/Month Sinoway Industrial Co., Ltd. Contact Supplier

77-52-1 Usage

Overview

Ursolic acid (UA) (3β-hydroxy-urs-12-en-28-oic-acid) (Fig. 1) is a pentacyclic triterpenoid carboxylic compound (C30H48O3) which may occur in the free acid form or as aglycones for triterpenoid saponins. Its isomer, oleanolic acid (OA) (3β-hydroxy-olea-12-en-28-oic-acid), presents different substitution of the methyl group, but they have similar molecular structures and pharmacological activity[1]. Oleanolic acid and ursolic acid are ubiquitous triterpenoids in plant kingdom, medicinal herbs, and are integral part of the human diet, once they are found in fruits and medicinal herbs. Figure 1 the chemical structure of Ursolic acid In recent years they became the subject of many publications because of their various activities and low toxicity. Many beneficial effects such as antioxidative, antimicrobial, anti-inflammatory, anticancer, anti-hyperlipidemic, analgesic, hepatoprotectory, gastroprotective, anti-ulcer, anti-HIV, cardiovascular, antiatherosclerotic and immunomodulatory effects have been reported[2, 3]. Several works have shown that the ursolic acid can also stimulate muscle growth, reduce fat gain and enhance the epidermal permeability barrier recovery in the skin[4], therefore it has been proposed as a skin therapeutic agent and it could be introduced in sport supplements[5], cosmetics[6] and health products[7].

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].

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.

References

Lim, S. W et al (2007). Journal of Dermatology, 34(9), 625–634. Kashyap, D., Tuli, H. S., & Sharma, A. K. (2016). Life Sciences,146, 201–213. Wo?niak, L., Sk?pska, S., & Marsza?ek, K. (2015). Molecules, 20(11), 20,614–20,641. Kunkel, S. D. et al (2012). PLoS ONE, 7(6)? Deane, C. S., et al (2017). American Journal of Physiology Endocrinology and Metabolism, 321(4), E282–E299. De Almeida et al (2014). Journal of Thermal Analysis and Calorimetry, 115(3), 2401–2406. Navina, R., Lee, Y. G., & Kim, S. M. (2017). Molecular biological roles of ursolic acid in he treatment of human diseases. Current Bioactive Compounds, 13(3), 177–185. Razborsek, M. I., Voncina, D. B., Dolecek, V., & Voncina, E. (2008). Determination of oleanolic, betulinic and ursolic acid in Lamiaceae and mass spectral fragmentation of their trimethylsilylated derivatives. Chromatographia, 67(5–6), 433–440 Silva, F. S. G., Oliveira, P. J., & Duarte, M. F. (2016). Oleanolic, ursolic, and betulinic acids as food supplements or pharmaceutical agents for type 2 diabetes: Promise or Illusion? Journal of Agricultural and Food Chemistry, 64, 2991–3008. Han, S. K., et al (2014). Oleanolic acid from Fragaria ananassa calyx leads to inhibition of alpha-MSH-induced melanogenesis in B16-F10 melanoma cells. Journal of the Korean Society for Applied Biological Chemistry, 57(6), 735–742 Kalogeropoulos, N., Yanni, A. E., Koutrotsios, G., & Aloupi, M. (2013). Toxicology, 55, 378–385. Zhang, F., Daimaru, E., Ohnishi, M., Kinoshita, M., & Tokuji, Y. (2013). Food Science and Technology Research, 19(1), 113–116. Guinda, á., Rada, M., Delgado, T., & Castellano, J. M. (2011). Pentacyclic triterpenic acids from Argania spinosa. European Journal of Lipid Science and Technology, 113(2), 231–237. Domingues, R. M. A., et al (2011). Cellulose Chemistry and Technology, 45(7–8), 475–481 Somova, L. I., Shode, F. O., & Mipando, M. (2004). Phytomedicine, 11, 121–129. Wójciak-Kosior, M., Sowaa, I., Kocjan, R., & Nowak, R. (2013). Industrial Crops and Products, 44, 373–377. Liu, J. (1995). Pharmacology of oleanolic acid and ursolic acid. Journal of Ethnopharmacology, 49, 57–68. Zhang, Y., Si, Y., et al (2016). Lipids, 51, 677–692. Dong, H., et al (2015). Biochemical Pharmacology, 93(2), 151–162. Wo?niak, L., Sk?pska, S., & Marsza?ek, K. (2015). Molecules, 20(11), 20,614–20,641 Lee, Y. H., Wang, E. X., Kumar, N., & Glickman, R. D. (2014). Ursolic acid differentially modulates apoptosis in skin melanoma and retinal pigment epithelial cells exposed to UV–VIS broadband radiation. Apoptosis, 19(5), 816–828. Gilabert, M., Marcinkevicius, K., Andújar, S., Schiavone, M., Arena, M. E., & Bardón, A. (2015). Sesquiand triterpenoids from the liverwort Lepidozia chordulifera inhibitors of bacterial biofilm and elastase activity of human pathogenic bacteria. Phytomedicine, 22(1), 77–85. Rodrigues, I. A., et al (2015). Natural products: Insights into Leishmaniasis inflammatory response. Mediators of Inflammation (Article number 835910). Jang, S. M., et al (2009). International Immunopharmacology, 9(1), 113–119. Takada, K., Nakane, T., Masuda, K., & Ishii, H. (2010). Phytomedicine, 17(14), 1114–1119 Kim, E. S., & Moon, A. (2015). Oncology Letters, 9(2), 897–902. Both, D. M., Goodtzova, K., Yarosh, D. B., & Brown, D. A. (2002) Archives of Dermatological Research, 293(11), 569–575 Gribble, G. W., Fu, L., Sporn, M. B., & Liby, K. T. (2015). Triterpenoids and compositions containing the same. USA Patent US 2015011627. Asami, C., & Lida, M. (2014). Lip cosmetics. Japan Patent JP 2014237594. Akamatsu, H., Suzuki, M., & Sakai, Y. (2007a). Cosmetic for improving skin barrier function. Japan Patent JP 2007161610. Akamatsu, H., Suzuki, M., & Sakai, Y. (2007b). Skin care preparation for improving skin barrier function. Japan Patent JP 200716161 Kobayashi, K., Imamura, H., & Seto, M. (2008). Skin care preparation containing antiinflammatory component. Japan Patent JP 2008115109. Ryu, S. H., et al (2013). Pharmaceutical composition comprising expression or activity inhibitor of TENC1 for preventing or treating diabetes mellitus. South Korea Patent KR 20130088054. Junhai, L., et al (2012). Methods for extracting ursolic acid from red jujube. China Patent CN 102321144. Anonymous (The inventor has waived the right to be mentioned). (2013). Ping, Z., Yong, L., & Chengbiao, X. (2011). Medical application of ursolic acid-NF (Nuclear Factor)-κB inhibitor. China Patent CN 102206243.

Description

Ursolic acid (77-52-1) inhibits endothelial cell proliferation and migration (IC50=5 μM) and angiogenesis.1?Promotes skeletal muscle rejuvenation via enhanced SIRT1 expression.2?Induces apoptosis in malignant mesothelioma cells.3

Chemical Properties

white to light yellow crystal powde

Uses

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

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.

Uses

Ursolic Acid is a Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.Ursolic acid protects against muscle atrophy and boosts muscle growth (see also tomatidine T538500).

Definition

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

General Description

Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial, anti-cancer, anti-oxidative and anti-inflammatory effects. It can also promote neuroregeneration after peripheral nerve injury. UA can enhance sleep duration by activating the GABAergic neurotransmitter system. [GABA= γ-aminobutyric acid]

Biochem/physiol Actions

Triterpenoid found in a variety of fruits, including apples. Cardioprotective and anti-tumor agent. Under study as a potential Alzheimer′s disease therapeutic due to its inhibitory effect on the interactions between amyloid-β and the CD36 receptor.

Anticancer Research

It is a triterpenoid, derived from basil, and suppresses the activation of NF-κB byinhibiting a kinase that activates NF-κB(IKK) (Aggarwal and Shishodia 2004). It suppresses tumorigenesis, tumor promotion, and angiogenesis by downregulationof the expression of lipoxygenases (LOX), MMP-9, and COX-2. It is reported toinduce apoptosis in breast cancer, melanoma, hepatoma, prostate cancer, andacute myelogenous leukemia by preventing replication of DNA, inhibition of proteintyrosine kinases, activation of caspases, induction of calcium release, anddownregulating apoptosis gene cellular inhibitor. Ursolic acid inhibits IκBαkinase activity, degradation of IκBα, phosphorylation, NF-κB-dependent reportergene expression, p65 nuclear translocation, and p65 phosphorylation. Inhibitionof NF-κB leads to the reduction of cyclin D1, COX-2, and MMP9 expression.This downregulates STAT-3 activation and its regulated gene products such ascyclin D1, Mcl-1, Bcl-xL, survivin, Bcl-2, and VEGF. It also induces the expressionof tyrosine phosphatase SHP-1 protein and of mRNA (Aggarwal et al. 2008;Hsu et al. 2004).

Cytotoxicity

IC50 (μg/mL): 6.7 (518A2), 5.3 (A2780), 7(A549), 6.4 (FaDu), 4.8 (HT29), 5.8(MCF-7), 8.5 (NIH3T3) (Wiemann et al.2016) IC50 (μg/mL): 12.38 (MGC-803),17.12(HCT-116), 13.39 (T24), 13.81(HepG2), 16.36 (A549), >45.7 (HL-7702)(Hua et al. 2015).

References

1) Sohn?et al.?(1995),?Anti-angiogenic activity of triterpene acids; Cancer Lett.,?94?213 2) Bakhtiari?et al.?(2016),?Short-term ursolic acid promotes skeletal muscle rejuvenation through enhancing of SIRT1 expression and satellite cells proliferation; Biomed. Pharmacother.,?78?185 3) Sohn?et al.?(2016),?Blockage of epithelial to mesenchymal transition and upregulation of let 7b are critically involved in ursolic acid induced apoptosis in malignant mesothelioma cell; J. Biol. Sci.,?12?1279
InChI:InChI=1/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)/p-1/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

77-52-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (U0065)  Ursolic Acid  >90.0%(GC) 77-52-1 100mg 490.00CNY Detail
TCI America (U0065)  Ursolic Acid  >90.0%(GC) 77-52-1 1g 1,990.00CNY Detail
Sigma-Aldrich (89797)  Ursolicacid  analytical standard 77-52-1 89797-5MG-F 1,056.51CNY Detail
Sigma-Aldrich (89797)  Ursolicacid  analytical standard 77-52-1 89797-25MG-F 4,189.77CNY Detail
Aldrich (U6753)  Ursolicacid  ≥90% 77-52-1 U6753-100MG 705.51CNY Detail
Aldrich (U6753)  Ursolicacid  ≥90% 77-52-1 U6753-500MG 2,416.05CNY Detail
Sigma-Aldrich (Y0001523)  Ursolicacid  European Pharmacopoeia (EP) Reference Standard 77-52-1 Y0001523 1,880.19CNY Detail
Sigma-Aldrich (03240595)  Ursolicacid  primary pharmaceutical reference standard 77-52-1 03240595-10MG 2,813.85CNY Detail
USP (1707770)  Ursolicacid  United States Pharmacopeia (USP) Reference Standard 77-52-1 1707770-25MG 4,647.24CNY Detail

77-52-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ursolic acid

1.2 Other means of identification

Product number -
Other names Urs-12-en-28-oic acid, 3-hydroxy-, (3β)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77-52-1 SDS

77-52-1Synthetic route

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With lithium In ethylenediamine for 4h; Heating;70%
phenyl-3β-acetoxy-urs-12-en-28-oate
104668-95-3

phenyl-3β-acetoxy-urs-12-en-28-oate

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol for 15h; Heating;1.33%
sodium acetate
127-09-3

sodium acetate

A

ursolic acid
77-52-1

ursolic acid

B

Oleanolic acid
508-02-1

Oleanolic acid

Conditions
ConditionsYield
With cultured cells of Rabdosia japonica Hara for 96h; Mechanism; labelling studies;
3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester

3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 4h; Heating;23 mg
3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate
1198208-27-3

3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,4-dioxane at 20℃; for 18h;
3-O-(β-D-glucopyranosyl)-ursolic acid 28-O-(β-D-glucopyranosyl) ester
28288-99-5

3-O-(β-D-glucopyranosyl)-ursolic acid 28-O-(β-D-glucopyranosyl) ester

A

D-glucose
50-99-7

D-glucose

B

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 2h; Reflux;
3β-hydroxyurs-12-en-28-oic acid 3-α-L-rhamnopyranoside
1038914-11-2

3β-hydroxyurs-12-en-28-oic acid 3-α-L-rhamnopyranoside

A

L-rhamnose
73-34-7

L-rhamnose

B

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 2h;
C36H56O9

C36H56O9

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With Helix pomatia β-glucuronidase; water In aq. acetate buffer at 37℃; for 4h; pH=5.27; Enzymatic reaction;
Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃;100%
In diethyl ether at 0℃; for 24h;98%
With diethyl ether
ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With Jones reagent; silica gel In acetone at 0℃; for 0.5h; Jones Oxidation;100%
With Jones reagent In acetone Cooling with ice;99%
With chromium(VI) oxide; sulfuric acid In acetone98%
ursolic acid
77-52-1

ursolic acid

acetic anhydride
108-24-7

acetic anhydride

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid
915-79-7, 7372-30-7, 94482-46-9, 105452-47-9, 121470-75-5

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid

Conditions
ConditionsYield
With pyridine100%
With pyridine at 20℃; for 24h;100%
With pyridine; dmap at 20℃; for 2.5h;97%
ursolic acid
77-52-1

ursolic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate
16684-20-1

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water for 8h; Heating;99%
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;90%
ursolic acid
77-52-1

ursolic acid

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;99%
Stage #1: ursolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 5h;
95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;95%
N-BOC-1,2-diaminoethane
57260-73-8

N-BOC-1,2-diaminoethane

ursolic acid
77-52-1

ursolic acid

C37H62N2O4

C37H62N2O4

Conditions
ConditionsYield
Stage #1: ursolic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
99%
Stage #1: ursolic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
95%
ursolic acid
77-52-1

ursolic acid

prenyl bromide
870-63-3

prenyl bromide

3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate
1198208-27-3

3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;98%
With potassium carbonate In acetone at 20℃;30%
With potassium carbonate In acetone at 20℃;
ursolic acid
77-52-1

ursolic acid

allyl bromide
106-95-6

allyl bromide

3-hydroxy-urs-12-en-28-oic acid allyl ester
1220960-77-9

3-hydroxy-urs-12-en-28-oic acid allyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;98%
Stage #1: ursolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 8h;
91%
With potassium carbonate In N,N-dimethyl-formamide for 24h;90.4%
Stage #1: ursolic acid With sodium hydroxide In acetone
Stage #2: allyl bromide In acetone at 70℃; for 4h;
10.1%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;
ursolic acid
77-52-1

ursolic acid

1-bromoacetone

1-bromoacetone

C33H52O4

C33H52O4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;98%
ursolic acid
77-52-1

ursolic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

Conditions
ConditionsYield
In methanol; benzene97%
In methanol; hexane; toluene at 20℃;95%
In methanol; benzene84.7%
In methanol
With methanol In hexane; benzene at 50℃; for 1.5h;66.3 mg
ursolic acid
77-52-1

ursolic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl ursolate

benzyl ursolate

Conditions
ConditionsYield
With potassium carbonate In acetone97%
ursolic acid
77-52-1

ursolic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
192211-41-9

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;97%
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water at 0 - 20℃; for 18h;93%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;92%
ursolic acid
77-52-1

ursolic acid

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
192211-41-9

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 2h;96%
With potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;95%
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;94%
ursolic acid
77-52-1

ursolic acid

Propargylamine
2450-71-7

Propargylamine

N-propargyl 3β-dihydroxyurs-12-en-28-amide

N-propargyl 3β-dihydroxyurs-12-en-28-amide

Conditions
ConditionsYield
Stage #1: ursolic acid With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: Propargylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;
96%
ursolic acid
77-52-1

ursolic acid

propargyl bromide
106-96-7

propargyl bromide

prop-2-yn-1-yl (1S,2R,4aS,6aS,6bR,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)carboxylate
1243271-20-6

prop-2-yn-1-yl (1S,2R,4aS,6aS,6bR,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;93%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 12h;93%
ursolic acid
77-52-1

ursolic acid

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

2-methoxy-2-oxoethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
1283594-24-0

2-methoxy-2-oxoethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;86.1%
methyl bromide
74-83-9

methyl bromide

ursolic acid
77-52-1

ursolic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h;95%
ursolic acid
77-52-1

ursolic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

ursolic acid metformin salt
1541169-42-9

ursolic acid metformin salt

Conditions
ConditionsYield
In acetonitrile for 16h;94%
ursolic acid
77-52-1

ursolic acid

1-(2-bromoethoxy)-4-nitrobenzene
13288-06-7

1-(2-bromoethoxy)-4-nitrobenzene

C38H55NO6
1446690-25-0

C38H55NO6

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;93%
ursolic acid
77-52-1

ursolic acid

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate
125700-67-6

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

1-benzotriazolyl 3β-dihydroxyurs-12-en-28-oate

1-benzotriazolyl 3β-dihydroxyurs-12-en-28-oate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;93%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;93%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h;
ursolic acid
77-52-1

ursolic acid

C10H24NO(1+)

C10H24NO(1+)

C40H70NO3(1+)

C40H70NO3(1+)

Conditions
ConditionsYield
With dmap In chloroform at 0℃; for 48h;93%
ursolic acid
77-52-1

ursolic acid

C13H30NO(1+)

C13H30NO(1+)

C43H76NO3(1+)

C43H76NO3(1+)

Conditions
ConditionsYield
With dmap In chloroform at -5℃; for 24h;93%
ursolic acid
77-52-1

ursolic acid

uvaol
545-46-0

uvaol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Reflux;92%
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Reflux; Inert atmosphere; Sealed tube;90.9%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 8h; Inert atmosphere; Reflux;15%
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