469-38-5

Basic information

• Product Name: CYCLOARTENOL
• Synonyms: 9,19-CYCLO-9BETA-LANOST-24-EN-3BETA-OL;9,19-CYCLO-9 BETA-LANOST-24-EN-3B-OL;24,(5-ALPHA)-CHOLESTEN-9-19-CYCLO-4,4,14-ALPHA-TRIMETHYL-3-BETA-OL;CYCLOARTENOL;CYCLOARTENOL(RG);9,19-Cyclolanost-24-en-3-ol;CYCLO-L-(L-PHE-L-PHE);9,19-Cyclolanosta-24-ene-3β-ol
• CAS NO: 469-38-5
• Molecular Formula: C30H50O
• Molecular Weight: 426.72
• Product Categories: Tri-Terpenoids;Building block
• Mol File: 469-38-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 115～117℃
• Boiling Point: 505.464 °C at 760 mmHg
• Flash Point: 221.931 °C
• Appearance: /
• Density: 1.01 g/cm³
• Vapor Pressure: 2.47E-12mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: -20°C Freezer
• Solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.14±0.70(Predicted)
• BRN: 2224850
• CAS DataBase Reference: CYCLOARTENOL(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOARTENOL(469-38-5)
• EPA Substance Registry System: CYCLOARTENOL(469-38-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 469-38-5(Hazardous Substances Data)

Usage

Uses

Cycloartenol is a triterpenoid used in eukaryotic steroid biosynthesis.

InChI:InChI=1/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1

Synthetic route

Cycloartenol (21238-33-5) → cycloartenol (469-38-5)

Conditions	Yield
With potassium hydroxide In ethanol for 4h; Heating;	94%
Alkaline hydrolysis;

cycloartenol acetate (1259-10-5) → cycloartenol (469-38-5)

Conditions	Yield
With potassium hydroxide In methanol Yield given;

Arundinol (136891-87-7) → cycloartenol (469-38-5)

Conditions	Yield
With sodium hydroxide for 4h; Heating;	0.02 g

2,3-Oxidosqualene (14050-42-1, 54910-48-4, 54910-49-5, 54910-50-8, 55058-26-9, 55058-27-0, 132199-42-9, 138809-21-9, 147731-51-9, 7200-26-2) → parkeol (514-45-4) + cycloartenol (469-38-5) + tirucallol (79-63-0)

Conditions	Yield
With CAS1Ile841Val mutant; YPG+heme rearrangement; cyclization;

oryzanol-A → cycloartenol (469-38-5)

Conditions	Yield
With potassium hydroxide

2,3-Oxidosqualene (14050-42-1, 54910-48-4, 54910-49-5, 54910-50-8, 55058-26-9, 55058-27-0, 132199-42-9, 138809-21-9, 147731-51-9, 7200-26-2) → cycloartenol (469-38-5)

Conditions	Yield
With Arabidopsis thaliana cycloartenol synthase Ile481Gly; Triton X-100 In phosphate buffer for 24h; pH=6.4; Product distribution; Further Variations:; Reagents; Cyclization; Enzymatic reaction;
With Pisum sativum cycloartenol synthase I365L mutant Reagent/catalyst;

squalene 2,3(S)-oxide (54910-48-4) → parkeol (514-45-4) + cycloartenol (469-38-5) + tirucallol (79-63-0)

Conditions	Yield
With cycloartenol synthase I481V mutant In phosphate buffer at 20℃; for 24h; pH=7.4; Product distribution; Further Variations:; Reagents;

methanol (67-56-1) + Cycloartenol (21238-33-5) → 24-methylenecycloartanol (1449-09-8, 13614-08-9, 118628-12-9) + cycloartenol (469-38-5)

Conditions	Yield
With sodium hydroxide; water In ethanol; isopropyl alcohol for 2h; Heating / reflux;

2,3-Oxidosqualene (14050-42-1, 54910-48-4, 54910-49-5, 54910-50-8, 55058-26-9, 55058-27-0, 132199-42-9, 138809-21-9, 147731-51-9, 7200-26-2) → cycloartenol (469-38-5) + 10α-cucurbita-5,24-diene-3β-ol (35012-08-9)

Conditions	Yield
With Pisum sativum cycloartenol synthase G617A mutant
With Pisum sativum cycloartenol synthase Y118L mutant

squalene 2,3(S)-oxide (54910-48-4) → cycloartenol (469-38-5)

Conditions	Yield
With cycloartenol synthase from leaves of Paris polyphylla Reagent/catalyst;

cycloartenol (469-38-5) + acetic anhydride (108-24-7) → cycloartenol acetate (1259-10-5)

Conditions	Yield
With pyridine for 15h; Ambient temperature;	98%
With pyridine
With pyridine

cycloartenol (469-38-5) → cycloartan-24,25-epoxy-3β-ol (26955-76-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 5h;	87%

cycloartenol (469-38-5) → cycloart-24-en-3-one (511-63-7) + cycloart-25-en-3b,24-diol (99946-06-2, 99946-09-5, 10388-48-4) + cycloartan-3β,24ξ,25-triol

Conditions	Yield
With Glomerella fusarioides IFO 8831 mycelium In methanol; dimethyl sulfoxide at 20℃; for 240h;	A 2.2% B 0.8% C 1%

cycloartenol (469-38-5) + benzoyl chloride (98-88-4) → 3β-benzoyloxy-9β,19-cyclo-lanost-24-ene (16763-82-9)

cycloartenol (469-38-5) → cycloartanol (4657-58-3)

Conditions	Yield
With hydrogen; acetic acid; platinum(IV) oxide
With hydrogen; platinum(IV) oxide In ethanol under 760 Torr; Ambient temperature;
With hydrogen; 5%-palladium/activated carbon In isopropyl alcohol at 50℃; under 2206.72 - 3677.86 Torr; for 6h;

cycloartenol (469-38-5) → parkeol (514-45-4) + tirucallol (79-63-0) + Cucurbita-5(10),24-dien-3β-ol (110654-88-1) + tirucalla-7,24-dien-3β-ol (23515-91-5)

Conditions	Yield
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Further byproducts given;

cycloartenol (469-38-5) → parkeol (514-45-4) + Cucurbita-5(10),24-dien-3β-ol (110654-88-1) + 10α-cucurbita-5,24-diene-3β-ol (35012-08-9) + tirucalla-7,24-dien-3β-ol (23515-91-5)

Conditions	Yield
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Further byproducts given;

cycloartenol (469-38-5) → 9,19-cyclolanostan-3-one (4936-10-1)

Conditions	Yield
With 4-methylisopropylbenzene; nickel Heating;
With pyridine; chromium(VI) oxide; hydrogen Multistep reaction;
Multi-step reaction with 2 steps 1: H2, AcOH / PtO2 2: CrO3, H2SO4 / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: p-cymene / Raney-Ni / Heating 2: H2 / PtO2 / acetic acid View Scheme

chloro-trimethyl-silane (75-77-4) + cycloartenol (469-38-5) → 4,4,14α-trimethyl-9β,19-cyclo-5α-cholest-24-en-3β-ol trimethylsilyl ether

Conditions	Yield
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane In hexane

cycloartenol (469-38-5) → cycloart-24-en-3-one (511-63-7)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In N,N-dimethyl-formamide
With 4-methylisopropylbenzene; nickel Heating;

cycloartenol (469-38-5) → cycloart-25-en-3-one (157523-40-5)

Conditions	Yield
With 4-methylisopropylbenzene; nickel Heating;

cycloartenol (469-38-5) → parkeol (514-45-4) + tirucallol (79-63-0) + Cucurbita-5(10),24-dien-3β-ol (110654-88-1) + 10α-cucurbita-5,24-diene-3β-ol (35012-08-9) + tirucalla-7,24-dien-3β-ol (23515-91-5) + 5α-Lanosta-9(11),25-dien-3β-ol (129763-89-9) + other alcohols, and dehydration products

Conditions	Yield
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Product distribution;

cycloartenol (469-38-5) + 4-ethoxycarbonyloxy-3-methoxy-trans-cinnamoyl chloride → 3β-(4-ethoxycarbonyloxy-3-methoxy-trans-cinnamoyloxy)-9β,19-cyclo-lanost-24-ene

Conditions	Yield
With pyridine

cycloartenol (469-38-5) + S-Adenosyl-L-methionine (14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6) → 24S/β-methyl-25-dehydrocycloartanol (511-61-5)

Conditions	Yield
With Prototheca wickerhamii YB4330 sterol methyl transferase at 35℃; for 0.75h; pH=7.5 - 8.0; Enzyme kinetics; Methylation;
With Prototheca wickerhamii YB4330 sterol methyl transferase Methylation;

cycloartenol (469-38-5) + S-adenosyl-L-[methyl-2H3]methionine (68684-40-2) → [28-2H3]cyclolaudenol

Conditions	Yield
With Prototheca wickerhamii YB4330 sterol methyl transferase at 35℃; for 0.75h; pH=7.5 - 8.0; Methylation;

cycloartenol (469-38-5) + S-Adenosyl-L-methionine (14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6) → 24-methylenecycloartanol (1449-09-8, 13614-08-9, 118628-12-9)

Conditions	Yield
With sterol methyl transferase at 35℃;
With plant sterol methyltransferase 1 Enzyme kinetics;

cycloartenol (469-38-5) → 25,26,27-trisnor-3β-hydroxy-cycloartan-24-al (152135-66-5)

Conditions	Yield
With ozone In dichloromethane at -78℃;

cycloartenol (469-38-5) → C30H48O3 (943985-79-3)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 87 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 5 h / 0 - 20 °C 2.1: sodium borohydride / ethanol / 0.17 h / 0 °C 2.2: 92 percent / acetic acid; ethanol / 5 h / 80 °C 3.1: 90 percent / aq. hydrogen peroxide; pyridine / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 66 percent / OsO4; NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 12 h 5.1: 70 percent / NaH / tetrahydrofuran; various solvent(s) / 1 h / -78 - 0 °C View Scheme

cycloartenol (469-38-5) → C36H56O2Se (943985-75-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 87 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 5 h / 0 - 20 °C 2.1: sodium borohydride / ethanol / 0.17 h / 0 °C 2.2: 92 percent / acetic acid; ethanol / 5 h / 80 °C View Scheme

cycloartenol (469-38-5) → C30H48O3

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 87 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 5 h / 0 - 20 °C 2.1: sodium borohydride / ethanol / 0.17 h / 0 °C 2.2: 92 percent / acetic acid; ethanol / 5 h / 80 °C 3.1: 90 percent / aq. hydrogen peroxide; pyridine / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 66 percent / OsO4; NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 12 h 5.1: 16 percent / NaH / tetrahydrofuran; various solvent(s) / 1 h / -78 - 0 °C View Scheme

cycloartenol (469-38-5) → (23Z)-9,19-cycloart-23-ene-3β,25-diol

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 87 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 5 h / 0 - 20 °C 2.1: sodium borohydride / ethanol / 0.17 h / 0 °C 2.2: 92 percent / acetic acid; ethanol / 5 h / 80 °C 3.1: 90 percent / aq. hydrogen peroxide; pyridine / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 66 percent / OsO4; NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 12 h 5.1: 70 percent / NaH / tetrahydrofuran; various solvent(s) / 1 h / -78 - 0 °C 6.1: 94 percent / diethyl ether / 2.5 h / -78 - 0 °C View Scheme

cycloartenol (469-38-5) → (R)-3-((3S,5R,8S,9S,10R,13R,14S,17R)-3-Hydroxy-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl)-butyraldehyde (33201-43-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 87 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 5 h / 0 - 20 °C 2.1: sodium borohydride / ethanol / 0.17 h / 0 °C 2.2: 92 percent / acetic acid; ethanol / 5 h / 80 °C 3.1: 90 percent / aq. hydrogen peroxide; pyridine / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 66 percent / OsO4; NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 12 h View Scheme
Multi-step reaction with 3 steps 1: O3 / CH2Cl2 / -78 °C 2: Et3N / CH2Cl2 / Heating 3: O3 / CH2Cl2 / -78 °C View Scheme

Upstream product

• 1259-10-5 cycloartenol acetate 
• 21238-33-5 Cycloartenol 
• 136891-87-7 Arundinol 
• 14050-42-1 2,3-Oxidosqualene 
• 54910-48-4 squalene 2,3(S)-oxide 
• 67-56-1 methanol 

Downstream Products

• 511-63-7 cycloart-24-en-3-one 
• 514-45-4 parkeol 
• 79-63-0 tirucallol 
• 110654-88-1 Cucurbita-5(10),24-dien-3β-ol 
• 35012-08-9 10α-cucurbita-5,24-diene-3β-ol 
• 23515-91-5 tirucalla-7,24-dien-3β-ol 
• 129763-89-9 5α-Lanosta-9(11),25-dien-3β-ol 
• 511-61-5 24S/β-methyl-25-dehydrocycloartanol 
• 107329-41-9 (24Ξ)-3β-benzoyloxy-24,25-dibromo-9β,19-cyclo-lanostane 
• 21238-33-5 Cycloartenol 
• 104204-19-5 3β-(3,4-dimethoxy-trans-cinnamoyloxy)-9β,19-cyclo-lanost-24-ene 
• 99946-06-2 cycloart-25-en-3b,24-diol 
• 54482-57-4 (23E)-25-hydroxycycloart-23-ene-3β,25-diol 
• 943985-75-9 C₃₆H₅₆O₂Se 

Relevant articles and documents

Enzyme redesign: Two mutations cooperate to convert cycloartenol synthase into an accurate lanosterol synthase

Efforts to modify the catalytic specificity of enzymes consistently show that it is easier to broaden the substrate or product specificity of an accurate enzyme than to restrict the selectivity of one that is promiscuous. Described herein are experiments in which cycloartenol synthase was redesigned to become a highly accurate lanosterol synthase. Several single mutants have been described that modify the catalytic specificity of cycloartenol to form some lanosterol. Modeling studies were undertaken to identify combinations of mutations that cooperate to decrease the formation of products other than lanosterol. A double mutant was constructed and characterized and was shown to cyclize oxidosqualene accurately to lanosterol (99%). This catalytic change entailed both relocating polarity with a His477Asn mutation and modifying steric constraints with an Ile481Val mutation. Copyright

Directed evolution to investigate steric control of enzymatic oxidosqualene cyclization. An isoleucine-to-valine mutation in cycloartenol synthase allows lanosterol and parkeol biosynthesis [9]

-

DRUGS, FOOD OR DRINK FOR IMPROVING PANCREATIC FUNCTIONS

Compounds having a cyclolanostane skeleton such as 9,19-cyclolanostan-3-ol and 24-methylene-9,19-cyclolanostan-3-ol are used as an active ingredient of a drug and food or drink for improving pancreatic functions.