EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

betulinic acid
(3b)-3-hydroxylup-20(29)-en-28-oic acid

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CAS Number: 472-15-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-448-8
FDA UNII: 4G6A18707N
Nikkaji Web:J11.885K
MDL:MFCD00009619
XlogP3-AA:8.20 (est)
Molecular Weight:456.71016000
Formula:C30 H48 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 550.02 °C. @ 760.00 mm Hg (est)
Flash Point: 573.00 °F. TCC ( 300.50 °C. ) (est)
logP (o/w): 7.653 (est)
Soluble in:
 water, 0.001607 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Betulinic acid 98%
BOC Sciences
For experimental / research use only.
Betulinic acid 0.98
Odor: characteristic
Use: betulinic acid is a pentacyclic lupane-type triterpene derivative of betulin with antiinflammatory, anti-HIV and antineoplastic activities.
ExtraSynthese
For experimental / research use only.
Betulinic acid (HPLC) ≥97%
Glentham Life Sciences
Betulinic acid
Jiangyin Healthway
Betulinic Acid
New functional food ingredients
Santa Cruz Biotechnology
For experimental / research use only.
Betulinic Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
Betulinic Acid technical grade, 90%
sds
Skyherb Technologies
Betulinic Acid 98%
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for betulinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for betulinic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :64971
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000472151
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):64971
Pubchem (sid):135022033
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08619
HMDB (The Human Metabolome Database):HMDB30094
FooDB:FDB001532
Export Tariff Code:2918.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 basil
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 bean winged bean root
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 chicory
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 elder black elder bark
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 eurya japonica bark
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 grape root
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 jackfruit root
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 jambul bark
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 jambul leaf
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 jambul stem bark
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 nance leaf
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 olive
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 persimmon
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 persimmon american persimmon
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 persimmon calyx
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 persimmon leaf
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 persimmon root
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 pomegranate
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 pomegranate bark
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 pomegranate leaf
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 rosemary
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 rosemary leaf
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 sacred garlic pear stem bark
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 walnut english walnut stem bark
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Synonyms:
 betulic acid
 betulinicacid
(3b)-3-hydroxylup-20(29)-en-28-oic acid
 

Articles:

PubMed:Chemical Constituents of Gold-red Apple and Their α-Glucosidase Inhibitory Activities.
PubMed:Molecular modeling of Ruellia tuberosa L compounds as a-amylase inhibitor: an in silico comparation between human and rat enzyme model.
PubMed:Phytochemicals and antioxidant activities of Rhus tripartitum (Ucria) fruits depending on locality and different stages of maturity.
PubMed:Contribution of phenolics and essential oils to the antioxidant and antimicrobial properties of Disporopsis pernyi (Hua) Diels.
PubMed: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.
PubMed:Chemical constituents of Rhododendron formosanum show pronounced growth inhibitory effect on non-small-cell lung carcinoma cells.
PubMed:Beneficial Effect of Betulinic Acid on Hyperglycemia via Suppression of Hepatic Glucose Production.
PubMed:Vitiquinolone--a quinolone alkaloid from Hibiscus vitifolius Linn.
PubMed:Ethanol extract of Lycopus lucidus elicits positive inotropic effect via activation of Ca2+ entry and Ca2+ release in beating rabbit atria.
PubMed:Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
PubMed:Synthesis and cytotoxic activity of new betulin and betulinic acid esters with conjugated linoleic acid (CLA).
PubMed:Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma.
PubMed:Betulinic acid alleviates non-alcoholic fatty liver by inhibiting SREBP1 activity via the AMPK-mTOR-SREBP signaling pathway.
PubMed:Unusual immuno-modulatory triterpene-caffeates in the skins of russeted varieties of apples and pears.
PubMed:Apoptosis of human breast cancer cells induced by microencapsulated betulinic acid from sour jujube fruits through the mitochondria transduction pathway.
PubMed:Combined treatment of betulinic acid, a PTP1B inhibitor, with Orthosiphon stamineus extract decreases body weight in high-fat-fed mice.
PubMed:Leptin: making it live up to its promise using natural products.
PubMed:Antidepressant-like effects of fractions, essential oil, carnosol and betulinic acid isolated from Rosmarinus officinalis L.
PubMed: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.
PubMed:Phytochemical profile of Rosmarinus officinalis and Salvia officinalis extracts and correlation to their antioxidant and anti-proliferative activity.
PubMed:A novel one-step microbial transformation of betulin to betulinic acid catalysed by Cunninghamella blakesleeana.
PubMed:Lignans and triterpenes from the root of Pseuderanthemum carruthersii var. atropurpureum.
PubMed:Exploration of the antiplatelet activity profile of betulinic acid on human platelets.
PubMed:Effect on tumor necrosis factor-α production and antioxidant ability of black alder, as factors related to its anti-inflammatory properties.
PubMed:Betulinic acid decreases ER-negative breast cancer cell growth in vitro and in vivo: role of Sp transcription factors and microRNA-27a:ZBTB10.
PubMed:Betulinic acid has an inhibitory effect on pancreatic lipase and induces adipocyte lipolysis.
PubMed:Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer.
PubMed:Identification and determination of carboxylic acids in food samples using 2-(2-(anthracen-10-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)ethyl 4-methylbenzenesulfonate (APIETS) as labeling reagent by HPLC with FLD and APCI/MS.
PubMed:Anti-inflammatory effects of seeds of the tropical fruit camu-camu (Myrciaria dubia).
PubMed:Development of a new HPLC method with precolumn fluorescent derivatization for rapid, selective and sensitive detection of triterpenic acids in fruits.
PubMed:Biotransformation optimization of betulin into betulinic acid production catalysed by cultured Armillaria luteo-virens Sacc ZJUQH100-6 cells.
PubMed:Isolation and structure determination of one new metabolite isolated from the red fermented rice of Monascus purpureus.
PubMed:Betulinic acid stimulates the differentiation and mineralization of osteoblastic MC3T3-E1 cells: involvement of BMP/Runx2 and beta-catenin signals.
PubMed:Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart.
PubMed:Betulinic acid, a natural pentacyclic triterpenoid, prevents abdominal fat accumulation in mice fed a high-fat diet.
PubMed:Betulinic acid: a natural product with anticancer activity.
PubMed:Triterpenic and other lipophilic components from industrial cork byproducts.
PubMed:Antiproliferative terpenoids from almond hulls (Prunus dulcis): identification and structure-activity relationships.
PubMed:Four new prenylated isoflavonoids in Tadehagi triquetrum.
PubMed:Quantitative analysis of anti-inflammatory and radical scavenging triterpenoid esters in evening primrose oil.
PubMed:Constituents in evening primrose oil with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities.
PubMed:Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
PubMed:Identification of three triterpenoids in almond hulls.
 
Notes:
isolated from bark of eurya japonica. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis.; Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53.
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