Melting point	13-15 ºC
Boiling point	129-130 ºC
Flash point	113 ºC
Density	1.117
Refractive index	1.564

Symbol(GHS)	Xi
Hazard Codes	R36/38
SDS/MSDS	S26;S36

Source	SDS/MSDS Samples
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Synthetic Route

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Articles

Peer-Reviewed Papers

Synthesis and biological evaluation of antitumor-active gamma-butyrolactone substituted betulin derivatives.René Csuk et al.Bioorganic & medicinal chemistry, 18(7), 2549-2558 (2010-03-20) Diterpenoid, steroid, and triterpenoid agonists of liver X receptors from diversified terrestrial plants and marine sources.Hiranthi Jayasuriya et al.Journal of natural products, 68(8), 1247-1252 (2005-08-30) Transcriptional profiles of the response of methicillin-resistant Staphylococcus aureus to pentacyclic triterpenoids.Pooi Yin Chung et al.PloS one, 8(2), e56687-e56687 (2013-02-26) Synthesis and biological evaluation of antitumour-active betulin derivatives.René Csuk et al.Bioorganic & medicinal chemistry, 18(3), 1344-1355 (2009-12-26) Two series of new semisynthetic triterpene derivatives: differences in anti-malarial activity, cytotoxicity and mechanism of action.Gloria N S da Silva et al.Malaria journal, 12, 89-89 (2013-03-19) Betulinic acid derivatives as HIV-1 antivirals.Christopher Aiken et al.Trends in molecular medicine, 11(1), 31-36 (2005-01-15) Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives.Sami Alakurtti et al.Bioorganic & medicinal chemistry, 18(4), 1573-1582 (2010-02-02) Betulinic acid enhanced the chemical sensitivity of esophageal cancer cells to cisplatin by inducing cell pyroptosis and reducing cell stemness.Jie Chen et al.Annals of palliative medicine, 9(4), 1912-1920 (2020-06-25) Betulinic acid isolated from Vitis amurensis root inhibits 3-isobutyl-1-methylxanthine induced melanogenesis via the regulation of MEK/ERK and PI3K/Akt pathways in B16F10 cells.Kyong-Suk Jin et al.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 68, 38-43 (2014-03-19) Bioactive oleanane, lupane and ursane triterpene acid derivatives.Maria de L e Silva et al.Molecules (Basel, Switzerland), 17(10), 12197-12205 (2012-10-19) Dipeptidyl peptidase IV inhibition potentiates amino acid- and bile acid-induced bicarbonate secretion in rat duodenum.Takuya Inoue et al.American journal of physiology. Gastrointestinal and liver physiology, 303(7), G810-G816 (2012-07-24) Suppression of STAT3 and HIF-1 alpha mediates anti-angiogenic activity of betulinic acid in hypoxic PC-3 prostate cancer cells.Jimin Shin et al.PloS one, 6(6), e21492-e21492 (2011-07-07) Hedgehog-Gli signaling pathway inhibitors as anticancer agents.Neeraj Mahindroo et al.Journal of medicinal chemistry, 52(13), 3829-3845 (2009-03-25) Betulin induces mitochondrial cytochrome c release associated apoptosis in human cancer cells.Yang Li et al.Molecular carcinogenesis, 49(7), 630-640 (2010-06-22) Novel triacsin C analogs as potential antivirals against rotavirus infections.Yunjeong Kim et al.European journal of medicinal chemistry, 50, 311-318 (2012-03-01) Influence of betulinic acid on lymphocyte subsets and humoral immune response in mice.Y Jine et al.Polish journal of veterinary sciences, 15(2), 305-313 (2012-08-01) Apoptosis of human breast cancer cells induced by microencapsulated betulinic acid from sour jujube fruits through the mitochondria transduction pathway.Yan-Fang Sun et al.Food chemistry, 138(2-3), 1998-2007 (2013-02-16) Purity-activity relationships of natural products: the case of anti-TB active ursolic acid.Birgit U Jaki et al.Journal of natural products, 71(10), 1742-1748 (2008-09-19) Functional Characterization of Cucurbitadienol Synthase and Triterpene Glycosyltransferase Involved in Biosynthesis of Mogrosides from Siraitia grosvenorii.Longhai Dai et al.Plant & cell physiology, 56(6), 1172-1182 (2015-03-12) Souroubea sympetala (Marcgraviaceae): a medicinal plant that exerts anxiolysis through interaction with the GABAA benzodiazepine receptor.Martha Mullally et al.Canadian journal of physiology and pharmacology, 92(9), 758-764 (2014-08-21) Antidepressant-like effects of fractions, essential oil, carnosol and betulinic acid isolated from Rosmarinus officinalis L.Daniele G Machado et al.Food chemistry, 136(2), 999-1005 (2012-11-06) Synthesis and antiplasmodial activity of betulinic acid and ursolic acid analogues.Adrine M Innocente et al.Molecules (Basel, Switzerland), 17(10), 12003-12014 (2012-10-23) Betulinic acid: a promising anticancer candidate.David A Eiznhamer et al.IDrugs : the investigational drugs journal, 7(4), 359-373 (2004-04-02) Betulinic acid prevention of d-galactosamine/lipopolysaccharide liver toxicity is triggered by activation of Bcl-2 and antioxidant mechanisms.Zhan-Wei Zheng et al.The Journal of pharmacy and pharmacology, 63(4), 572-578 (2011-03-16) Bioactive constituents of the stem bark of Beilschmiedia zenkeri.Bruno Ndjakou Lenta et al.Journal of natural products, 72(12), 2130-2134 (2009-11-13) Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana.Ki Hyun Kim et al.Bioorganic & medicinal chemistry letters, 20(6), 1944-1947 (2010-02-24) Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.Chih-Chun Wen et al.Journal of medicinal chemistry, 50(17), 4087-4095 (2007-08-01) Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.Kyoko Nakagawa-Goto et al.Bioorganic & medicinal chemistry letters, 19(13), 3378-3381 (2009-06-02) Betulinic acid inhibits superoxide anion-mediated impairment of endothelium-dependent relaxation in rat aortas.Ling-Bo Qian et al.Indian journal of pharmacology, 44(5), 588-592 (2012-11-01) Inhibitory effect of Careya arborea on inflammatory biomarkers in carrageenan-induced inflammation.Rayhana Begum et al.Pharmaceutical biology, 53(3), 437-445 (2014-12-05) Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.Cédric Genet et al.Journal of medicinal chemistry, 53(1), 178-190 (2009-11-17) Betulinic acid induces Bax/Bak-independent cytochrome c release in human nasopharyngeal carcinoma cells.Liu Y, Luo W. Molecular Cell, 33, 517-524 (2012) Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.Xiaoan Wen et al.Journal of medicinal chemistry, 51(12), 3540-3554 (2008-06-04) Anticancer activity of betulinic acid on MCF-7 tumors in nude mice.Archana A Damle et al.Indian journal of experimental biology, 51(7), 485-491 (2013-08-01) Determination of betulinic acid, oleanolic acid and ursolic acid from Achyranthes aspera L. using RP-UFLC-DAD analysis and evaluation of various parameters for their optimum yield.Sandeep R Pai et al.Indian journal of experimental biology, 54(3), 196-202 (2016-05-06) Betulinic acid exerts immunoregulation and anti-tumor effect on cervical carcinoma (U14) tumor-bearing mice.Peijun Wang et al.Die Pharmazie, 67(8), 733-739 (2012-09-11) Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds.Sara Hoet et al.Journal of natural products, 70(8), 1360-1363 (2007-07-20) Sulfonoquinovosyl diacylglyceride selectively targets acute lymphoblastic leukemia cells and exerts potent anti-leukemic effects in vivo.Chetan Kumar Jain et al.Scientific reports, 5, 12082-12082 (2015-07-21) NOXA as critical mediator for drug combinations in polychemotherapy.H Ehrhardt et al.Cell death & disease, 3, e327-e327 (2012-06-22) Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives.Yi Bi et al.Bioorganic & medicinal chemistry letters, 17(5), 1475-1478 (2007-02-06) Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products.Charles Gauthier et al.Bioorganic & medicinal chemistry letters, 19(8), 2310-2314 (2009-03-17) Betulinic acid decreases specificity protein 1 (Sp1) level via increasing the sumoylation of sp1 to inhibit lung cancer growth.Tsung-I Hsu et al.Molecular pharmacology, 82(6), 1115-1128 (2012-09-08) Betulinic acid selectively increases protein degradation and enhances prostate cancer-specific apoptosis: possible role for inhibition of deubiquitinase activity.Teresita Reiner et al.PloS one, 8(2), e56234-e56234 (2013-02-21) Betulinic acid ameliorates endothelium-dependent relaxation in L-NAME-induced hypertensive rats by reducing oxidative stress.Fu JY, Qian LB, Zhu LG, Liang HT, et al. European Journal of Pharmaceutical Sciences, 44, 385-391 (2012) Betulinic acid alleviates non-alcoholic fatty liver by inhibiting SREBP1 activity via the AMPK-mTOR-SREBP signaling pathway.Hai Yan Quan et al.Biochemical pharmacology, 85(9), 1330-1340 (2013-02-26) Central muscarinic cholinergic activation alters interaction between splenic dendritic cell and CD4+CD25- T cells in experimental colitis.Peris Munyaka et al.PloS one, 9(10), e109272-e109272 (2014-10-09) Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues.Sven Sommerwerk et al.Bioorganic & medicinal chemistry, 23(17), 5595-5602 (2015-07-28) Betulinic acid and its derivatives: a review on their biological properties.Perumal Yogeeswari et al.Current medicinal chemistry, 12(6), 657-666 (2005-03-26) Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants.Zhao Dang et al.Bioorganic & medicinal chemistry letters, 22(16), 5190-5194 (2012-07-24) Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.Midori A Arai et al.Bioorganic & medicinal chemistry, 16(21), 9420-9424 (2008-10-10) Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies.Zhongjie Liang et al.European journal of medicinal chemistry, 46(6), 2011-2021 (2011-03-29) Interactions of pentacyclic triterpene acids with cardiolipins and related phosphatidylglycerols in model systems.Marcin Broniatowski et al.Biochimica et biophysica acta, 1838(10), 2530-2538 (2014-06-08) Investigation of antimalarial activity, cytotoxicity and action mechanism of piperazine derivatives of betulinic acid.Gloria N S Silva et al.Tropical medicine & international health : TM & IH, 20(1), 29-39 (2014-10-14) Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors.Zhao Dang et al.Journal of medicinal chemistry, 52(23), 7887-7891 (2009-06-17) Adsorption between TC-stabilized AuNPs and the phosphate group: application of the PTP1B activity assay.Jun Lv et al.The Analyst, 140(23), 8017-8022 (2015-11-03) Targeting mitochondrial apoptosis by betulinic acid in human cancers.Simone Fulda et al.Drug discovery today, 14(17-18), 885-890 (2009-06-13) Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins.Charles Gauthier et al.Journal of natural products, 72(1), 72-81 (2009-01-01) Betulinic acid derivatives as anticancer agents: structure activity relationship.Rama Mukherjee et al.Anti-cancer agents in medicinal chemistry, 6(3), 271-279 (2006-05-23) The effects of a TGR5 agonist and a dipeptidyl peptidase IV inhibitor on dextran sulfate sodium-induced colitis in mice.Taisuke Sakanaka et al.Journal of gastroenterology and hepatology, 30 Suppl 1, 60-65 (2015-04-02) Simultaneous HPTLC analysis of ursolic acid, betulinic acid, stigmasterol and lupeol for the identification of four medicinal plants commonly available in the Indian market as Shankhpushpi.Neeraj Kumar Sethiya et al.Journal of chromatographic science, 53(5), 816-823 (2014-09-14) Betulinic acid, a natural compound with potent anticancer effects.Franziska B Mullauer et al.Anti-cancer drugs, 21(3), 215-227 (2010-01-16) Isolation of cytotoxic metabolites from targeted peruvian amazonian medicinal plants.José C Aponte et al.Journal of natural products, 71(1), 102-105 (2008-01-01) alpha-Glucosidase inhibitory activity of triterpenoids from Cichorium intybus.Atta-ur-Rahman et al.Journal of natural products, 71(5), 910-913 (2008-03-18) [Chemical constituents of Dolomiaea souliei].Hu Wei et al.Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 37(9), 1249-1253 (2012-07-19) Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.Kuo-Hsiung Lee Journal of natural products, 73(3), 500-516 (2010-03-02) Betulinic acid delivered in liposomes reduces growth of human lung and colon cancers in mice without causing systemic toxicity.Franziska B Mullauer et al.Anti-cancer drugs, 22(3), 223-233 (2011-01-26) Combined treatment of betulinic acid, a PTP1B inhibitor, with Orthosiphon stamineus extract decreases body weight in high-fat-fed mice.Yoon-Jung Choi et al.Journal of medicinal food, 16(1), 2-8 (2012-12-22) Analysis of triterpenoids and phytosterols in vegetables by thin-layer chromatography coupled to tandem mass spectrometry.Katerina Naumoska et al.Journal of chromatography. A, 1381, 229-238 (2015-01-20) Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity.Rita C Santos et al.Bioorganic & medicinal chemistry, 17(17), 6241-6250 (2009-08-14) Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.Liwei Fu et al.Journal of natural products, 68(2), 198-206 (2005-02-26) HIF-1A and C/EBPs transcriptionally regulate adipogenic differentiation of bone marrow-derived MSCs in hypoxia.Chen Jiang et al.Stem cell research & therapy, 6, 21-21 (2015-04-19) Triterpenoid pyrazines and benzopyrazines with cytotoxic activity.Milan Urban et al.Journal of natural products, 70(4), 526-532 (2007-03-21) Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones.Ali Koohang et al.Bioorganic & medicinal chemistry letters, 19(8), 2168-2171 (2009-03-17) Limnophilaspiroketone, a highly oxygenated phenolic derivative from Limnophila geoffrayi.Dae Sik Jang et al.Journal of natural products, 68(7), 1134-1136 (2005-07-26) Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.Do Thi Ha et al.Bioorganic & medicinal chemistry letters, 19(19), 5556-5559 (2009-09-01) Betulinic acid: a natural product with anticancer activity.Simone Fulda Molecular nutrition & food research, 53(1), 140-146 (2008-12-10) Betulin-derived compounds as inhibitors of alphavirus replication.Leena Pohjala et al.Journal of natural products, 72(11), 1917-1926 (2009-10-21) Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.Denis Fourches et al.Chemical research in toxicology, 23(1), 171-183 (2009-12-18) Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.Teresa Mencherini et al.Journal of natural products, 74(10), 2116-2121 (2011-10-01) Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines.Liqiong Fang et al.Journal of natural products, 69(3), 332-337 (2006-03-28) Hepatoprotective potential of Tecomella undulata stem bark is partially due to the presence of betulinic acid.Mahendra Jain et al.Journal of ethnopharmacology, 143(1), 194-200 (2012-07-14) A simple GC-MS method for the screening of betulinic, corosolic, maslinic, oleanolic and ursolic acid contents in commercial botanicals used as food supplement ingredients.Augusta Caligiani et al.Food chemistry, 136(2), 735-741 (2012-11-06) Synthesis and structure-activity relationship study of novel cytotoxic carbamate and N-acylheterocyclic bearing derivatives of betulin and betulinic acid.Rita C Santos et al.Bioorganic & medicinal chemistry, 18(12), 4385-4396 (2010-05-25) Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection.Robert H Cichewicz et al.Medicinal research reviews, 24(1), 90-114 (2003-11-05) Heparanase is a host enzyme required for herpes simplex virus-1 release from cells.Satvik R Hadigal et al.Nature communications, 6, 6985-6985 (2015-04-29) Exploration of the antiplatelet activity profile of betulinic acid on human platelets.Andreas G Tzakos et al.Journal of agricultural and food chemistry, 60(28), 6977-6983 (2012-06-23) Leptin: making it live up to its promise using natural products.Sunmin Park et al.Journal of medicinal food, 16(1), 1-1 (2012-12-22) Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells.Malgorzata Drag-Zalesinska et al.Bioorganic & medicinal chemistry letters, 19(16), 4814-4817 (2009-06-30) Synthesis, proapoptotic screening, and structure-activity relationships of novel aza-lupane triterpenoids.Aye Aye Mar et al.Bioorganic & medicinal chemistry letters, 20(18), 5389-5393 (2010-08-20) A simple and visible colorimetric method through Zr(4+)-phosphate coordination for the assay of protein tyrosine phosphatase 1B and screening of its inhibitors.Juan Zhang et al.The Analyst, 140(16), 5716-5723 (2015-07-15) Anti-inflammatory, antimicrobial and antioxidant activities of Diospyros bipindensis (Gürke) extracts and its main constituents.I Cesari et al.Journal of ethnopharmacology, 146(1), 264-270 (2013-01-22) Betulinic acid negates oxidative lung injury in surgical sepsis model.Madhu C Lingaraju et al.The Journal of surgical research, 193(2), 856-867 (2014-10-09) Lupane-type triterpenoids from Microtropis fokienensis and Perrottetia arisanensis and the apoptotic effect of 28-hydroxy-3-oxo-lup-20(29)-en-30-al.I-Hsiao Chen et al.Journal of natural products, 71(8), 1352-1357 (2008-07-02) The natural product betulinic acid rapidly promotes amyloid-β fibril formation at the expense of soluble oligomers.Matthew S Planchard et al.ACS chemical neuroscience, 3(11), 900-908 (2013-02-13) Inhibitors of DNA polymerase beta: activity and mechanism.Zhijie Gao et al.Bioorganic & medicinal chemistry, 16(8), 4331-4340 (2008-03-18) Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.Charles Gauthier et al.Bioorganic & medicinal chemistry, 17(5), 2002-2008 (2009-02-10) Antiproliferative triterpenes from Melaleuca ericifolia.Fatma M Abdel Bar et al.Journal of natural products, 71(10), 1787-1790 (2008-10-02) Synthesis, cytotoxicity and liposome preparation of 28-acetylenic betulin derivatives.René Csuk et al.Bioorganic & medicinal chemistry, 18(20), 7252-7259 (2010-09-18) Bioactive Phytochemicals from Wild Arbutus unedo L. Berries from Different Locations in Portugal: Quantification of Lipophilic Components.Daniela F S Fonseca et al.International journal of molecular sciences, 16(6), 14194-14209 (2015-06-26) Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties.Harish Kommera et al.European journal of medicinal chemistry, 45(8), 3346-3353 (2010-05-18) GDC-0941 enhances the lysosomal compartment via TFEB and primes glioblastoma cells to lysosomal membrane permeabilization and cell death.Stefanie Enzenmüller et al.Cancer letters, 329(1), 27-36 (2012-09-25) A novel one-step microbial transformation of betulin to betulinic acid catalysed by Cunninghamella blakesleeana.Yu Feng et al.Food chemistry, 136(1), 73-79 (2012-09-29) Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida.Yulin Ren et al.Journal of natural products, 73(5), 949-955 (2010-04-14) Betulin-betulinic acid natural product based analogs as anti-cancer agents.Subash C Jonnalagadda et al.Anti-cancer agents in medicinal chemistry, 13(10), 1477-1499 (2013-07-16) Synthesis and cytotoxic activity of new betulin and betulinic acid esters with conjugated linoleic acid (CLA).Barbara Tubek et al.Natural product communications, 8(4), 435-438 (2013-06-07) Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives.Vivek Kumar et al.Bioorganic & medicinal chemistry letters, 18(18), 5058-5062 (2008-08-30) Betulinic acid attenuates lung injury by modulation of inflammatory cytokine response in experimentally-induced polymicrobial sepsis in mice.Madhu Cholenahalli Lingaraju et al.Cytokine, 71(1), 101-108 (2014-10-04) Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease.Peter Šilhár et al.Bioorganic & medicinal chemistry letters, 21(8), 2229-2231 (2011-03-23) Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.Harish Kommera et al.Bioorganic & medicinal chemistry letters, 20(11), 3409-3412 (2010-05-11) Simultaneous Determination of Oleanolic and Ursolic Acids in Rat Plasma by HPLC-MS: Application to a Pharmacokinetic Study After Oral Administration of Different Combinations of QingGanSanJie Decoction Extracts.Liang Zhao et al.Journal of chromatographic science, 53(7), 1185-1192 (2015-02-11) Rational design and semisynthesis of betulinic acid analogues as potent topoisomerase inhibitors.Fatma M Abdel Bar et al.Journal of natural products, 72(9), 1643-1650 (2009-08-21) Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A.Tadashi Honda et al.Bioorganic & medicinal chemistry letters, 16(24), 6306-6309 (2006-09-26)

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