Calenduladiol

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Basic information

CAS: 10070-48-1
Standard SMILES: C=C(C)[C@@H]1CC[C@@]2(C)[C@H]1[C@H]1CC[C@@H]3[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@@H]2O
InChIKey: AJBZENLMTKDAEK-SKESNUHASA-N
Molecular formula: C30H50O2
Average molar mass: 442.7 g/mol
Monoisotopic mass: 442.38108083

Overview

Calenduladiol has been reported in Beyeria leschenaultii, Chuquiraga erinacea, and Pulicaria canariensis with data available.

Names & identifiers

Preferred name: Calenduladiol
IUPAC: (1R,3aS,4S,5aR,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]chrysene-4,9-diol
English name: CALENDULADIOL
Molecular formula: C30H50O2
Molecular weight: 442.7168

Names & synonyms

CalenduladiolThurberinUNII-5F669S8218NSC 922275F669S8218NSC-92227NSC-133914(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta(a)chrysene-4,9-diol(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysene-4,9-diolLUP-20(29)-ENE-3beta,16beta-DIOLRefChem:30922LUP-20(30)-ENE-3beta,16beta-DIOL

Show more names

Lup-20(29)-ene-3β,16β-diolLup-20(29)-ene-3,16-diol, (3β,16β)-Lup-20(29)-ene-3,16-diol, (3β,16β)- (9CI)

10070-48-1Lup-20(29)-ene-3,16-diol, (3beta,16beta)-NSC92227orb1697973SCHEMBL1251536BDBM50019002AKOS040750991LUP-20(29)-ENE-3.BETA.,16.BETA.-DIOL

Database identifiers

CAS: 10070-48-1
PubChem CID: 461835
ChEMBL: CHEMBL462795
UNII: 5F669S8218
Nikkaji: J15.660D

Properties

Computed structural properties

XLogP: 8.3
Topological polar surface area: 40.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 32
Formal charge: 0
Complexity: 801

Physicochemical properties

Melting point: 218 · 218-219 °C
Boiling point: 518.1 · 518.1±33.0 °C(Predicted)
Density: 1.021 · 1.021±0.06 g/cm3(Predicted)
pka: 14.88 · 14.88±0.70(Predicted)
FDA UNII: 5 F669S8218 · 5F669S8218
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 280 · P280-P305+P351+P338

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

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications

UsesCalenduladiol is a new triterpene diol from Calendula officinalis flowers. Calenduladiol is a triterpenoid that possesses valuable potential medicinal properties ranging from anti-microbial to anti-cancer properties.

Upstream & downstream products

Downstream products

5α-Lupan-3β-ol

Related reactions

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Compound notes

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