HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Lup-20(29)-en-3-ol, (3beta)-

HCID 73040
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
545-47-1
Standard SMILES
C=C(C)[C@@H]1CC[C@]2(C)CCC3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
InChIKey
MQYXUWHLBZFQQO-JGGBMTAGSA-N
Molecular formula
C30H50O
Average molar mass
426.7 g/mol
Monoisotopic mass
426.38616621

Names & identifiers

Preferred name
Lup-20(29)-en-3-ol, (3beta)-
IUPAC
(1R,3aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
English name
Lupeol
Molecular formula
C30H50O
Molecular weight
426.73

Names & synonyms

Lup-20(29)-en-3-ol, (3.beta.)-SCHEMBL561024(1R,3aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol(1R,3aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-olLupenolFAGARASTEROLLupeLUPEOLLupinolClerodolB-VISCOLMONOGYNOL
Show more names
NSC 90487LUPEOL(P)

Database identifiers

CAS
545-47-1
PubChem CID
73040

Properties

Computed structural properties

XLogP
9.9
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
31
Formal charge
0
Complexity
766

Physicochemical properties

Melting point
215 ° · 215°
alpha
20 · D20 +27.2° (c = 4.8 in chloroform)
Boiling point
482.1 °C · 482.1°C (rough estimate)
Density
0.9457 · 0.9457
refractive index
1.491 · 1.4910 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
15.19 · 15.19±0.70(Predicted)
color
White to Off-White
optical activity
26.42 · +26.420 (c 3.51, CHCl3)
Cosmetics Ingredients Functions
SKIN CONDITIONING
InChIKey
MQYXUWHLBZFQQO-QGTGJCAVSA-N
SMILES
[H]C12CCC3C4(C)CCC(O)C(C)(C)[C@]4([H])CCC3(C)[C@]1(C)CCC5(C)CC[C@H](C(C)=C)[C@]25[H]
LogP
10.46 · 10.460 (est)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
OK5763000
hs_code
29061990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501
Hazardous Substances Data
545-47-1(Hazardous Substances Data)

Chemistry & industry

Applications · 5 items

DescriptionLupeol is a kind of novel anti-inflammatory and anti-cancer dietary triterpene that can be found in white cabbage, green pepper, strawberry, olive, mangoes and grapes. In recent years, much progress has been made on the application of this molecule for clinical treatment of various kind of disorders. On the one hand, it has been extensively studied that it is capable of inhibiting inflammation under both in vitro and in animal models. Studies have shown that Lupeol is a multi-target agent during its anti-inflammation effect, targeting on many key molecular pathways involving nuclear factor kappa B (NFκB), cFLIP, Fas, Kras, phosphatidylinositol-3-kinase (PI3K)/Akt and Wnt/β-catenin. On the other hand, Lupeol has strong anti-tumor effect during treatment of various cancer types such as prostate, skin, pancreatic and breast cancer. The anti-tumor effect might be related to its potential to modulate important signaling pathways such as nuclear factor kappa B (NFκB) and the phosphatidylinositol 3-kinase [PI3K] /Akt (protein kinase B pathway), which are crucial during tumorigenesis.

Usesantineoplastic

UsesLupeol was used as reference standard in method development and validation of lupeol from Vernonia Cinerea using HPLC method. It has been used as a standard for the identification and quantification of triterpenoids in blueberry cuticular wax by GC.

UsesAbundant plant triterpene. Occurs in the skin of lupin seeds, in circle, in the latex of fig trees and of rubber plants. It was detected in cocoons of Bombyx mori.

General DescriptionLupeol is a novel anti-cancer and anti-inflammatory dietary triterpene. They help in stabilizing phospholipid bilayers in plant cell membranes. In general, this group contains 28-29 carbons along with carbon-carbon double bonds, usually one in the sterol nucleus and at times a second in the alkyl side chain.

Upstream & downstream products

Downstream products

psi-taraxasterolalpha-Amyrin5α-Lupan-3β-ol

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS DataBase Reference
545 · 545-47-1(CAS DataBase Reference)
FDA UNII
268 W13H3O · O268W13H3O
NIST Chemistry Reference
Lupeol(545-47-1)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
24 · 24/25
WGK Germany
2 · 2
RTECS
5763000 · OK5763000
HS Code
29061990 · 29061990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Hazardous Substances Data
545 · 545-47-1(Hazardous Substances Data)

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017; +8613259417953 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海波以尔化工有限公司[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
潍坊华植生物科技有限公司17388075642 13815430202 · [email protected]
南京春秋生物工程有限公司17388075642 13815430202 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
杭州东帆化学有限公司86-0571-85151182
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
西安康诺化工有限公司029-86107037 15829389671 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in m ny edible fruits and vegetables.