CAS No.77-06-5,Gibberellic acid Suppliers

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Basic Information

Molecular Structure:
CAS No.:	77-06-5
Name:	Gibberellic acid
Article Data:	10
Cas Database

Formula:	C₁₉H₂₂O₆
Molecular Weight:	346.38
Synonyms:	Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone;4a,1-(epoxymethano)-7,9a-methanobenz[a]azulene-10-carboxylic acid, 1,2,4b,5,6,7,8,9,10,10a-decahydro-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-;Activol GA;Monopotassium 2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylate 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-;Gibberellic acid (GA3);2beta,4aalpha,7-Trihydroxy-1beta-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;2,4a, 7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-carboxylic acid 1-4-lactone;Pgr-iv;Monopotassium gibberellate;Gibrescol;GA3;Pro-Gibb Plus;Gibefol;Gib-Tabs;EPA Pesticide Chemical Code 043802;(1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadec-13-ene-9-carboxylic acid;Grocel;Acide gibberellique [ISO-French];Gibb-3-ene-1,10-dicarboxylic acid, 2,4a, 7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha., 2.beta.,4a.alpha.,4b.beta.,10.beta.)-;Ralex;Regulex;Gibberellic acid ( GA3 );Giberillic acid;Gibberellic-acid;Gibberellic acid (GA3 );Activol;Gibberellins;EPA Pesticide Chemical Code 043801;2beta,4alpha,7-Trihydroxy-1-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Brellin;Gibberellic acid GA3;Ryzup;Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, monopotassium salt, (1alpha,2beta,4aalpha,4bbeta,10beta)-;NCI-C55823;2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;Berelex;Gibberellin A3;2beta,4alpha,7-Trihydroxy-1-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Gib-Sol;Gibberellin X;Gibberellin;Gibberellinsaeure;Pro-Gibb;Release LC;Maxon (plant growth regulator);Gibberellins A4A7;Cekugib;Gibrofit;
EINECS:	201-001-0
Density:	1.49 g/cm³
Melting Point:	227 °C
Boiling Point:	628.6 °C at 760 mmHg
Flash Point:	231.4 °C
Solubility:	5 g/L (20 °C) in water
Appearance:	white powder
Hazard Symbols:	Xi
Risk Codes:	36
Safety:	26-36
Transport Information:	N/A
PSA:	104.06000
LogP:	1.02710

Synthetic route

: 19123-33-2
2β,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1α,10β-dicarboxylic acid 10,10'-anhydride 1->4a;1'->4'a-dilactone

A: 54878-53-4
GA3-7-alkohol

B: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; Yield given;	A 72% B n/a
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; other conditions; Yields of byproduct given;	A 72% B n/a

: 5087-25-2, 58917-17-2
gibberellin A3-ketone

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride

: 19147-54-7, 65563-70-4
Diacetyl-gibberellinsaeure

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 23℃; for 4h;

: 561-56-8
gibberellin A5

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
With air; alpha-ketoglute dipotassium; potassium ascorbate; iron(II) sulfate In various solvent(s) at 30℃; for 2h; enzyme preparation from anthers of Oryza sativa L., pH 8.0; Yield given;

: 53060-60-9
ent-7α-hydroxykaurene

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
With Giberella fujikuroi at 25℃; for 24h; incubation;

: 54878-55-6
0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PDC / dimethylformamide / 3.5 h / 23 °C 2: NaOCH3 / dimethylformamide / 4 h / 23 °C View Scheme

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

A: 427-79-2, 13613-87-1, 19123-39-8, 26688-43-7, 28862-60-4, 38045-67-9
allogibberic acid

B: 13613-87-1
(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions

Conditions	Yield
With sodium carbonate at 240℃; Product distribution; 1-5 min;	A n/a B 100%
With sodium carbonate at 240℃; 1-5 min;	A n/a B 100%
With hydrazine

: 108-24-7
acetic anhydride

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

: 19147-54-7, 65563-70-4
Diacetyl-gibberellinsaeure

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Cooling with ice; Inert atmosphere;	99%
With pyridine Ambient temperature;	2.0 g

: 821-41-0
5-Hexen-1-ol

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

: C25H32O6

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	99%

: 77-06-5
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

: 74-88-4
methyl iodide

: 510-50-9
gibberellic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone	98%
With potassium carbonate In acetone at 20℃; Inert atmosphere;	95.4%
With potassium carbonate In acetone at 18℃; for 20h;	94%
With potassium carbonate In acetone	92%
With cesium fluoride In N,N-dimethyl-formamide for 24h; Ambient temperature;	407 mg

Downstream Products

468-44-0

510-75-8

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Chemistry

Empirical Formula: C₁₉H₂₂O₆
Molecular Weight: 346.3744
EINECS: 201-001-0
Structure of Gibberellic Acid (CAS NO.77-06-5):

Index of Refraction: 1.661
Molar Refractivity: 85.786 cm3
Molar Volume: 231.972 cm3
Polarizability: 34.008 10-24cm3
Surface Tension: 71.863 dyne/cm
Density: 1.493 g/cm3
Flash Point: 231.438 °C
Enthalpy of Vaporization: 106.599 kJ/mol
Melting Point: 227 °C
Boiling Point: 628.595 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Storage temp: 0-6°C
Water Solubility: 5 g/L (20 º C)
Stability: Stable. Combustible. Incompatible with acids, strong oxidizing agents.
Product Categories: FINE Chemical & INTERMEDIATES; Plant Oils, Toxins, Phenolic Acids & Derivatives; Biochemistry; Plant Growth Regulators; Plant Growth Trgulators (Others); Antibiotic Explorer
Synonyms of Gibberellic Acid (CAS NO.77-06-5): (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone ; (3S,3aR,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-
methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno(1,2-b)furan-4-carboxylic acid ; Activol ; Berelex ; Brellin ; CCRIS 4820 ; Caswell No. 467 ; Cekugib ; Gibberellin ; Gibberellin A3 ; Gibefol ; Gibrescol ; Gibreskol ; Grocel ; Pro-Gibb Plus ; Regulex ; Ryzup

Uses

Gibberellic acid has the main following uses:

1.Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since Gibberellic acid regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. It is usually used in concentrations between 0.01-10 mg/L.
2.Gibberellic acid is a simple gibberellin, promoting growth and elongation of cells.

3.Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant. It is also widely used in the grape-growing industry as a hormone to induce the production of larger bundles and bigger grapes, especially Thompson seedless grapes, and in the Okanagan and Creston Valley it is used in the cherry industry as a growth regulator.

Toxicity Data With Reference

1.	dnd-sal:spr 1 mmol/L	PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
2.	dnd-mam:lym 1 mmol/L	PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
3.	orl-mus TDLo:142 g/kg/78W-I:ETA	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB223-159 .
4.	orl-rat LD50:6300 mg/kg	85ARAE Agricultural Chemicals, Books I, II, III, and IV. 3 (1976/77),43.

Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36
R36:Irritating to eyes.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: LY8990000
F: 10
HS Code: 29322980
Hazardous Substances Data 77-06-5(Hazardous Substances Data)
Mildly toxic by ingestion of gibberellic acid . It is showed to be questionable carcinogen by experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

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