Methyl abietate supplier | CasNO.127-25-3

Name
METHYL ABIETATE
EINECS
CAS No. 127-25-3
Article Data47
CAS DataBase
Density 1.02g/cm³
Solubility 17μg/L at 25℃
Melting Point <25 °C
Formula C21H32 O2
Boiling Point 403.8°Cat760mmHg
Molecular Weight 316.484
Flash Point 192.8°C
Transport Information
Appearance
Safety Low toxicity by ingestion and skin contact. A skin irritant. Probably slightly toxic. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Phenanthrenecarboxylicacid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-,methyl ester, [1R-(1a,4ab,4ba,10aa)]-; Abietic acid methyl ester (6CI,7CI); Podocarpa-7,13-dien-15-oic acid,13-isopropyl-, methyl ester (8CI); Methyl abietate; NSC 2141
PSA 26.30000
LogP 5.29460

Synthetic route

: 186581-53-3, 908094-01-9
diazomethane

: 514-10-3
abietic acid

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
In diethyl ether at 0℃;	100%
In diethyl ether at 0℃; for 0.166667h;	99%
With diethyl ether

: 514-10-3
abietic acid

: 77-78-1
dimethyl sulfate

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
With lithium hydroxide In N,N-dimethyl-formamide	100%
With lithium hydroxide In N,N-dimethyl-formamide	100%
With potassium carbonate In acetone at 20℃;	100%

: 514-10-3
abietic acid

: 616-38-6
carbonic acid dimethyl ester

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In N,N-dimethyl-formamide at 93 - 100℃; Reagent/catalyst; Concentration; Inert atmosphere;	99.6%

: 514-10-3
abietic acid

: 74-88-4
methyl iodide

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 14h; Reflux;	99%
With potassium carbonate In acetone for 12h; Reflux;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	81%

: 514-10-3
abietic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
In methanol; diethyl ether; toluene at 20℃; for 0.5h;	94%

: 67-71-0
dimethylsulfone

: 514-10-3
abietic acid

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
With lithium hydroxide In N,N-dimethyl-formamide at 20℃; for 16h;	86%

: 67-56-1
methanol

: 514-10-3
abietic acid

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
Stage #1: abietic acid With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 0.0833333h; Garegg-Samuelsson type reaction; Stage #2: methanol In dichloromethane at 20℃; Garegg-Samuelsson type reaction;	84%
With sulfuric acid for 36h; Heating;	45%
at 260 - 285℃; under 56634.1 - 88260.9 Torr;
With sulfuric acid

: 67-56-1
methanol

: 19897-44-0
7,13-Abietadien-18-oic acid anhydride

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
With sulfuric acid In benzene at 65℃; for 30h; Esterification;	49%

: 67-56-1
methanol

A: 127-25-3
methyl abietate

B: 25236-84-4
<1R-(1α,4aβ,4bα,6α,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-6-methoxy-7-(1-methylethyl)-phenanthrenecarboxylic acid methylester

C: <1R-(1α,4aβ,4bα,6β,10aα)>-1,2,3,4,4a,5,6,10,10a-decahydro-1,4a-dimethyl-6-methoxy-7-(1-methylethyl)-phenanthrenecarboxylic acid methylester

Conditions

Conditions	Yield
With iodine; copper dichloride; iron tricarbonyl 1) dibutylether, 3 d, heating, 2) diethylether, 2 h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;	A 1.5% B n/a C n/a
With iodine; copper dichloride; iron tricarbonyl 1) dibutylether, 3 days, heating, 2) diethylether, 2 h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;	A 1.5% B n/a C n/a

...Expand

: 77-78-1
dimethyl sulfate

potassium-salt of/the/ abietic acid: potassium-salt of/the/ abietic acid

: 127-25-3
methyl abietate

: 14351-66-7
abietic acid sodium salt

: 127-25-3
methyl abietate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 11 h / 25 °C 2: 49 percent / H2SO4 / benzene / 30 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / 3 h / 20 °C 2: 49 percent / H2SO4 / benzene / 30 h / 65 °C View Scheme

: 127-25-3
methyl abietate

: 666-84-2
abietinol

Conditions

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 6.5h; Ambient temperature;	100%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h;	99%
With lithium aluminium tetrahydride In diethyl ether for 0.666667h; Reduction; Heating;	98%

: 127-25-3
methyl abietate

: 228863-80-7
methyl <1aR(1aβ,2aα,3α,6aβ,7α,7aβ)>-decahydro-7a-peroxyformtacetal-7-<(4-methyl-3-oxoketal)pentyl>-3,6a-dimethylnaphth<2,3-b>oxiran-3-carboxylate

Conditions

Conditions	Yield
With pyridine; oxygen; ozone In dichloromethane at -70℃;	92%
With ozone In dichloromethane at -78℃;	78%

: 108-31-6
maleic anhydride

: 127-25-3
methyl abietate

: 54868-63-2
maleopimaric acid methyl ester

Conditions

Conditions	Yield
Stage #1: methyl abietate at 180℃; for 3h; Inert atmosphere; Stage #2: maleic anhydride With toluene-4-sulfonic acid; acetic acid for 12h; Diels-Alder reaction; Reflux;	90%
With zeolite NIC-2β In toluene for 7h; Heating;	0.04 g
With zeolite NIC-2β In toluene for 7h; Product distribution; Heating; also with α-methylacrolein or acrolein; var. catalysts, solvents;	0.04 g

: 127-25-3
methyl abietate

: 1235-74-1, 1757-97-7, 2756-34-5, 7151-00-0, 10178-27-5, 10178-29-7, 21699-55-8, 24035-60-7
Methyl dehydroabietate

Conditions

Conditions	Yield
With 5% Pd(II)/C(eggshell) at 240 - 250℃; Neat (no solvent);	85%
With palladium on activated charcoal at 240℃; Inert atmosphere;	85%
With aluminum oxide; palladium/alumina at 230℃;
With magnesium hydrosilicate; palladium at 230℃;
With palladium on activated charcoal at 240℃; for 3h;

: 127-25-3
methyl abietate

: 22552-63-2
methyl 13β,14β-dihydroxyabieta-7-en-18-oate

Conditions

Conditions	Yield
With pyridine; potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide In acetone for 168h; Reflux; regioselective reaction;	85%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In tert-butyl alcohol for 168h; Inert atmosphere; Reflux; regioselective reaction;	70%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 24h; Product distribution; Heating; var. ratios of the educt;	68%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 24h; Heating;	68%

: 127-25-3
methyl abietate

: 514-10-3
abietic acid

Conditions

Conditions	Yield
With Me2AlTeMe In toluene at 23℃; for 8h;	85%

: 127-25-3
methyl abietate

: 369387-06-4
methyl 7-hydroxy-13-isopropylpodocarpe-8,11,13-trien-15-oate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; selenium(IV) oxide In octane; dichloromethane for 12h;	83%

: 127-25-3
methyl abietate

: 228863-82-9
methyl <1aR(1aβ,2aα,3α,6aβ,7α,7aβ)>-decahydro-7a-formyl-7-(4-methyl-3-oxopentyl)-3,6a-dimethylnaphth<2,3-b>oxiran-3-carboxylate

Conditions

Conditions	Yield
With pyridine; oxygen; ozone In methanol at -70℃;	79%
Multi-step reaction with 2 steps 1: 78 percent / ozone / CH2Cl2 / -78 °C 2: 80 percent / triphenylphosphine / CH2Cl2 / 12 h / Ambient temperature View Scheme

: 127-25-3
methyl abietate

: 108-24-7
acetic anhydride

: 22565-68-0
methyl (1R,4aS,9R,10aR)-9-acetoxy-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)phenanthrene-1-carboxylate

Conditions

Conditions	Yield
With selenium(IV) oxide for 3h; Ambient temperature;	68%

: 127-25-3
methyl abietate

: 762-42-5
dimethyl acetylenedicarboxylate

: (Z)-2-((1R,4aS,9R,10aR)-7-Isopropyl-1-methoxycarbonyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl)-but-2-enedioic acid dimethyl ester

Conditions

Conditions	Yield
at 210℃; under 60004.8 - 86256.9 Torr; for 25h;	60%

: 127-25-3
methyl abietate

: 92215-39-9
methyl 7-oxoabiet-13(14)-ene-18-oate

Conditions

Conditions	Yield
With water; iodine; potassium hydrogencarbonate In diethyl ether at 20℃; for 24h; Inert atmosphere;	60%

: 127-25-3
methyl abietate

: 19402-34-7
methyl abieta-8,13(15)-dien-18-oate

Conditions

Conditions	Yield
Stage #1: methyl abietate With hydrogen bromide In acetic acid for 20h; Stage #2: With lithium hydroxide In N,N-dimethyl-formamide at 80℃; for 16h; Heating;	56%
Multi-step reaction with 2 steps 1: 47 percent / 33percent HBr / acetic acid / 6 h / Ambient temperature 2: 71 percent / lithium hydroxide monohydrate / dimethylformamide / 3.5 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 35 percent / 37percent HBr / acetic acid / 6.5 h / Ambient temperature 2: 74 percent / LiOH*H2O / dimethylformamide / 3.5 h / 80 °C View Scheme

: 127-25-3
methyl abietate

A: 13082-81-0
9-hydroxy-13-isopropyl-podocarpadien-(7.13)-oic acid-(15)-methyl ester

B: 17751-34-7
7,8-Dihydro-7β-hydroxy-8,9,10,11-dehydroabietinsaeure-methylester

Conditions

Conditions	Yield
With selenium(IV) oxide In acetonitrile for 24h;	A 48% B 32%

: 127-25-3
methyl abietate

A: 1802-09-1
methyl 7-hydroxy-13-isopropylpodocarpe-8,11,13-trien-15-oate

B: 17751-34-7
7,8-Dihydro-7β-hydroxy-8,9,10,11-dehydroabietinsaeure-methylester

Conditions

Conditions	Yield
With selenium(IV) oxide In acetonitrile for 24h;	A 48% B 32%

: 127-25-3
methyl abietate

A: 92215-39-9
[1R,(1α,4αβ,4βα,8αβ,10αα)]-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-1-phenanthrenecarboxylic acid methyl ester

B: 55177-17-8
(1aS,3aR,4R,7aR,7bR,9aS)-9a-Isopropyl-4,7a-dimethyl-1a,3,3a,4,5,6,7,7a,7b,8,9,9a-dodecahydro-1-oxa-cyclopropa[a]phenanthrene-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With iodine; potassium hydrogencarbonate In diethyl ether; water at 30℃; for 3h;	A 48% B n/a

: 127-25-3
methyl abietate

: 22628-83-7
methyl 8,15-dibromoabietan-18-oate

Conditions

Conditions	Yield
With hydrogen bromide In acetic acid for 6h; Ambient temperature;	47%
With hydrogen bromide In acetic acid for 6.5h; Ambient temperature;	35%

: 127-25-3
methyl abietate

: 925-90-6
ethylmagnesium bromide

: C22H34O

Conditions

Conditions	Yield
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 20℃; for 4h; Inert atmosphere;	47%

: 127-25-3
methyl abietate

: 546-67-8
lead(IV) tetraacetate

A: 1235-74-1, 1757-97-7, 2756-34-5, 7151-00-0, 10178-27-5, 10178-29-7, 21699-55-8, 24035-60-7
Methyl dehydroabietate

B: 22565-68-0
methyl (1R,4aS,9R,10aR)-9-acetoxy-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)phenanthrene-1-carboxylate

C: 127488-29-3
(1R,4aS,4bS,10aR)-4b-Acetoxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
In acetic acid at 80℃; for 7h;	A 37% B 43% C 17%

...Expand

: 127-25-3
methyl abietate

: 920-37-6
2-Chloroacrylonitrile

: 155507-60-1
Methyl 17,19-dinoratis-14-chloro-14-cyano-15-ene-16-(1-methylethyl)-4-carboxylate

Conditions

Conditions	Yield
With 10H-phenothiazine at 170℃; for 15h;	39%

: 127-25-3
methyl abietate

: 69226-51-3
2,2,2-trichloroethyl sulfamate

: methyl 7-(((2,2,2-trichloroethoxy)sulfonyl)amino)-8,11,13-abietatrien-18-oate

Conditions

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; bis(tertbutylcarbonyloxy)iodobenzene In benzene at 23℃; stereoselective reaction;	36%

: 127-25-3
methyl abietate

A: 18178-76-2
methyl 7β,14β-dihydroxy-13-isopropyl-8-podocarpan-15α-oate

B: 18125-91-2
methyl 7β-Hydroxy-13α-isopropylpodocarp-8(14)-en-15α-oate

C: methyl 7β-Hydroxy-13-isopropyl-8β-podocarp-13(14)-en-15α-oate

D: methyl 14β-Hydroxy-13α-isopropylpodocarp-7(8)-en-15α-oate

Conditions

Conditions	Yield
Stage #1: methyl abietate With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 3.5h; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium acetate In tetrahydrofuran; water for 16h; Inert atmosphere;	A 26% B 22% C 10% D 34%

...Expand

: 127-25-3
methyl abietate

A: 1235-74-1, 1757-97-7, 2756-34-5, 7151-00-0, 10178-27-5, 10178-29-7, 21699-55-8, 24035-60-7
Methyl dehydroabietate

B: 13082-81-0
9-hydroxy-13-isopropyl-podocarpadien-(7.13)-oic acid-(15)-methyl ester

C: 1802-09-1
methyl 7-hydroxy-13-isopropylpodocarpe-8,11,13-trien-15-oate

D: 17751-34-7
7,8-Dihydro-7β-hydroxy-8,9,10,11-dehydroabietinsaeure-methylester

Conditions

Conditions	Yield
With selenium(IV) oxide In carbon disulfide for 24h; Ambient temperature;	A 16% B 30% C 10% D 9%
With selenium(IV) oxide In 1,4-dioxane for 24h; Product distribution; Ambient temperature; various solvents (C6H6, CS2, Et2O, MeCN, t-BuOH, Ac2O); oxidation with lead tetraacetate;	A 17% B 29% C 17% D 18%

...Expand

Methyl abietate Chemical Properties

IUPAC: Methyl(1R,4aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate
Methyl abietate (127-25-3) is also called for 4-09-00-02176 (Beilstein Handbook Reference) ; AI3-01745 ; Abietic acid, methyl ester ; BRN 2702228 ; EINECS 204-832-7 ; Methyl 7,13-abietadien-18-oate ; NSC 2141 ; 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R,4aR,4bR,10aR)- ; 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R-(1alpha,4abeta,4balpha,10aalpha))- ; Podocarpa-7,13-dien-15-oic acid, 13-isopropyl-, methyl ester and so on.
Molecular Formula: C₂₁H₃₂O₂
Molecular Weight: 316.48
EINECS: 204-832-7
LogP: ACD/LogP: 6.93
ACD/LogD (pH 5.5): 6.93
ACD/LogD (pH 7.4): 6.93
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Heavy Atom Count: 23
Formal Charge: 0
Complexity: 556
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 2
Undefined Atom StereoCenter Count: 2
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.521
Molar Refractivity: 94.32 cm³
Surface Tension: 36.8 dyne/cm
Density: 1.02 g/cm³
Flash Point: 192.8°C
Enthalpy of Vaporization: 65.52 kJ/mol
Boiling Point: 403.8°C at 760 mmHg
The appearance of Methyl abietate (127-25-3) is colorless to yellow liquid boiling at 365°C.
The molecular structure of Methyl abietate (127-25-3) :

Methyl abietate Uses

Methyl abietate (127-25-3) is used as a solvent and plasticizer for lacquers, varnishes, and coatings.

Methyl abietate Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 12, Pg. 931, 1974.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 12, Pg. 931, 1974.

Methyl abietate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl abietate Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. Probably slightly toxic. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Product Name

METHYL ABIETATE

Synthetic route

Methyl abietate Chemical Properties

Methyl abietate Uses

Methyl abietate Toxicity Data With Reference

Methyl abietate Consensus Reports

Methyl abietate Safety Profile

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