9,19-Cyclolanost-24-en-3-ol, (3beta)- supplier

Name
CYCLOARTENOL
EINECS
CAS No. 469-38-5
Article Data11
CAS DataBase
Density 1.01 g/cm³
Solubility
Melting Point 115～117℃
Formula C₃₀H₅₀O
Boiling Point 505.464 °C at 760 mmHg
Molecular Weight 426.726
Flash Point 221.931 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 9,19-Cyclo-9b-lanost-24-en-3b-ol (8CI);Cycloartenol (6CI);9,19-Cyclo-24-lanosten-3b-ol;Cycloart-24-en-3b-ol;Handianol;NSC 670193;
PSA 20.23000
LogP 8.16890

Synthetic route

: 21238-33-5
Cycloartenol

: 469-38-5
cycloartenol

Conditions

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

: 1259-10-5
cycloartenol acetate

: 469-38-5
cycloartenol

Conditions

Conditions	Yield
With potassium hydroxide In methanol Yield given;

: 136891-87-7
Arundinol

: 469-38-5
cycloartenol

Conditions

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

: 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
2,3-Oxidosqualene

A: 514-45-4
parkeol

B: 469-38-5
cycloartenol

C: 79-63-0
tirucallol

Conditions

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

...Expand

oryzanol-A: oryzanol-A

: 469-38-5
cycloartenol

Conditions

Conditions	Yield
With potassium hydroxide

: 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
2,3-Oxidosqualene

: 469-38-5
cycloartenol

Conditions

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;

: 54910-48-4
squalene 2,3(S)-oxide

A: 514-45-4
parkeol

B: 469-38-5
cycloartenol

C: 79-63-0
tirucallol

Conditions

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

...Expand

: 67-56-1
methanol

: 21238-33-5
Cycloartenol

A: 1449-09-8, 13614-08-9, 118628-12-9
24-methylenecycloartanol

B: 469-38-5
cycloartenol

Conditions

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

...Expand

: 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
2,3-Oxidosqualene

A: 469-38-5
cycloartenol

B: 35012-08-9
10α-cucurbita-5,24-diene-3β-ol

Conditions

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

: 54910-48-4
squalene 2,3(S)-oxide

: 469-38-5
cycloartenol

Conditions

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

: 469-38-5
cycloartenol

: 108-24-7
acetic anhydride

: 1259-10-5
cycloartenol acetate

Conditions

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

: 469-38-5
cycloartenol

: 26955-76-0
cycloartan-24,25-epoxy-3β-ol

Conditions

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

: 469-38-5
cycloartenol

A: 511-63-7
cycloart-24-en-3-one

B: 99946-06-2, 99946-09-5, 10388-48-4
cycloart-25-en-3b,24-diol

C: cycloartan-3β,24ξ,25-triol

Conditions

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

...Expand

: 469-38-5
cycloartenol

: 98-88-4
benzoyl chloride

: 16763-82-9
3β-benzoyloxy-9β,19-cyclo-lanost-24-ene

: 469-38-5
cycloartenol

: 4657-58-3
cycloartanol

Conditions

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;

: 469-38-5
cycloartenol

A: 514-45-4
parkeol

B: 79-63-0
tirucallol

C: 110654-88-1
Cucurbita-5(10),24-dien-3β-ol

D: 23515-91-5
tirucalla-7,24-dien-3β-ol

Conditions

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

...Expand

: 469-38-5
cycloartenol

A: 514-45-4
parkeol

B: 110654-88-1
Cucurbita-5(10),24-dien-3β-ol

C: 35012-08-9
10α-cucurbita-5,24-diene-3β-ol

D: 23515-91-5
tirucalla-7,24-dien-3β-ol

Conditions

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

...Expand

: 469-38-5
cycloartenol

: 4936-10-1
9,19-cyclolanostan-3-one

Conditions

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

: 75-77-4
chloro-trimethyl-silane

: 469-38-5
cycloartenol

: 4,4,14α-trimethyl-9β,19-cyclo-5α-cholest-24-en-3β-ol trimethylsilyl ether

Conditions

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

: 469-38-5
cycloartenol

: 511-63-7
cycloart-24-en-3-one

Conditions

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

: 469-38-5
cycloartenol

: 157523-40-5
cycloart-25-en-3-one

Conditions

Conditions	Yield
With 4-methylisopropylbenzene; nickel Heating;

: 469-38-5
cycloartenol

A: 514-45-4
parkeol

B: 79-63-0
tirucallol

C: 110654-88-1
Cucurbita-5(10),24-dien-3β-ol

D: 35012-08-9
10α-cucurbita-5,24-diene-3β-ol

E: 23515-91-5
tirucalla-7,24-dien-3β-ol

F: 129763-89-9
5α-Lanosta-9(11),25-dien-3β-ol

G other alcohols, and dehydration products: other alcohols, and dehydration products

Conditions

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

...Expand

: 469-38-5
cycloartenol

4-ethoxycarbonyloxy-3-methoxy-trans-cinnamoyl chloride: 4-ethoxycarbonyloxy-3-methoxy-trans-cinnamoyl chloride

: 3β-(4-ethoxycarbonyloxy-3-methoxy-trans-cinnamoyloxy)-9β,19-cyclo-lanost-24-ene

Conditions

Conditions	Yield
With pyridine

: 469-38-5
cycloartenol

: 14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6
S-Adenosyl-L-methionine

: 511-61-5
24S/β-methyl-25-dehydrocycloartanol

Conditions

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;

: 469-38-5
cycloartenol

: 68684-40-2
S-adenosyl-L-[methyl-2H3]methionine

: [28-2H3]cyclolaudenol

Conditions

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

: 469-38-5
cycloartenol

: 14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6
S-Adenosyl-L-methionine

: 1449-09-8, 13614-08-9, 118628-12-9
24-methylenecycloartanol

Conditions

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

: 469-38-5
cycloartenol

: 152135-66-5
25,26,27-trisnor-3β-hydroxy-cycloartan-24-al

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃;

: 469-38-5
cycloartenol

: 943985-79-3
C30H48O3

Conditions

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

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

: 469-38-5
cycloartenol

: 943985-75-9
C36H56O2Se

Conditions

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

: 469-38-5
cycloartenol

: C30H48O3

Conditions

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

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

: 469-38-5
cycloartenol

: (23Z)-9,19-cycloart-23-ene-3β,25-diol

Conditions

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

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

: 469-38-5
cycloartenol

: 33201-43-3
(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

Conditions

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

9,19-Cyclolanost-24-en-3-ol, (3beta)- Specification

This chemical is called 9,19-Cyclolanost-24-en-3-ol, (3beta)-, and it can also be named as Cycloartenol. With the molecular formula of C₃₀H₅₀O, its molecular weight is 426.72. The CAS registry number of this chemical is 469-38-5. Additionally, its product category is Tri-Terpenoids.

Other characteristics of the 9,19-Cyclolanost-24-en-3-ol, (3beta)- can be summarised as followings: (1)ACD/LogP: 10.31; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 10.305; (4)ACD/LogD (pH 7.4): 10.305; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 9617628; (8)ACD/KOC (pH 7.4): 9617628; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 20.23 Å²; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 131.892 cm³; (15)Molar Volume: 421.038 cm³; (16)Polarizability: 52.286×10^-24cm³; (17)Surface Tension: 39.656 dyne/cm; (18)Density: 1.013 g/cm³; (19)Flash Point: 221.931 °C; (20)Enthalpy of Vaporization: 89.25 kJ/mol; (21)Boiling Point: 505.464 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Production method of this chemical: The 9,19-Cyclolanost-24-en-3-ol, (3beta)- could be obtained by the reactant of 3β-(4-hydroxy-3-methoxy-trans-cinnamoyloxy)-9β,19-cyclo-lanost-24-ene. This reaction needs the reagent of 10N aq. KOH, and the solvent of ethanol. The yield is 94 %. In addition, this reaction should be taken for 4 hours. The other condition is heating.

Uses of this chemical: The 9,19-Cyclolanost-24-en-3-ol, (3beta)- could react with acetic acid anhydride, and obtain the 3b-acetoxy-9b,19-cyclo-lanost-24-ene. This reaction needs the reagent of pyridine. The yield is 98 %. In addition, this reaction should be taken for 15 hours at the ambient temperature.

When you are using this chemical, please be cautious about it as the following: Do not breathe dust. Avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
1.SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O)C)C
2.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
3.InChIKey: ONQRKEUAIJMULO-YBXTVTTCBS

Product Name

CYCLOARTENOL

Synthetic route

9,19-Cyclolanost-24-en-3-ol, (3beta)- Specification

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