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77-06-5 Usage

Description

Gibberellic acid (GA) is a tetracyclic di-terpenoid compound. It is one of the major hormones that can be synthesized in plants and fungi. It has various kinds of physiological effects including stimulating seed germination, inducing mitotic division of the leaves, triggering transitions from meristem to shoot growth, vegetative to flowering, determining sex expression and grain development through crosstalk with many environmental signals such as light, temperature and water. In lab and greenhouse, it can be used to trigger germination of seeds which has previously remained dormant. It can also used to induce the production of larger amount and bigger grapes, boosting the grape industry. In industry, GA can be produced from Solid-state Fermentation (SSF) which can have relatively high yield.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 77-06-5 differently. You can refer to the following data:
1. Gibberellic Acid is a a pentacyclic diterpene acid. Gibberellic Acid is a hormone that is found in plants which promotes the growth and elongation of cells. Gibberellic acid acts as a plant growth reg ulator on account of its physiological and morphological effects in extremely low concentrations. Generally Gibberellic acid affects only the plant parts above the soil surface.
2. Gibberellic acid is used as a plant growth hormone. It is also used to trigger germination in dormant seeds in laboratory and green house settings and to stimulate rapid stem and root growth and induce mitotic division in the leaves of some plants. It also serves in grape growing industry as a hormone to induce the production of larger bundles and bigger grape.

General Description

White powder.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

Gibberellic acid is readily degraded by acids. .

Fire Hazard

Flash point data for Gibberellic acid are not available. Gibberellic acid is probably combustible.

Agricultural Uses

Different sources of media describe the Agricultural Uses of 77-06-5 differently. You can refer to the following data:
1. Plant growth hormone, Plant regulator: Gibberellic acids (Gibberellins) are naturally occurring plant hormones that are used as plant growth regulators to stimulate both cell division and elongation that affects leaves and stems. Applications of this hormone also hastens plant maturation and seed germination. Delayed harvesting of fruits, allowing them to grow larger. Gibberellic acids are applied to growing field crops, small fruits, grapes, vines and tree fruit, and ornamentals, shrubs and vines.
2. Gibberellic acid is an organic acid used as a plant growth hormone. It is formed by the fungus Gibberellafujikuroi in aerated submerged culture.
3. Gibberellin is a growth promoting substance found widely in plants. It was first isolated from the fungus Gibberella. Gibberellin increases the rate of photosynthesis and helps in the elongation of cells. It promotes the flowering and germination of plants. With a general formula of Cl9H22O6, gibberellins are also produced by Azotobacter, Azospirillum, etc.

Trade name

ACTIVOL?; BERELEX?; BRELLIN?; BOLL-SET?; CEKUGIB?; CROP BOOSTER?; CYTOPLEX HMS?, DYNOGEN?; FALGRO?; FLORALTONE? (with 2,3,5-triiodobenzoic acid); FLORGIB?; FOLI-ZYME?; GIBBEX?; GIBBERELLIN A 3 ?; GIBBERELLIN X?; GIBBREL?; GIBGRO?; GIB-SOL?; GIB-TABS?; GIBRESCOL?; GROCEL?; KALGIBB?; MAXON?; N-LARGE?; NOVAGIB?; PGR-IV?; PRO-GIBB?; REGULEX?; RELEASE?; RELAX?; RYZUP?; STIMULATE?; VIGOR?

Biochem/physiol Actions

Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.

Safety Profile

Mildly toxic by ingestion. Questionable carcinogen with experimental tumorigenic data. hlutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

It crystallises from EtOAc, EtOAc/pet ether, MeOH/pet ether or Me2CO/pet ether. [Cross J Chem Soc 3022 1960, Beilstein 18 III/IV 6533.]

References

https://en.wikipedia.org/wiki/Gibberellic_acid https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4002599/

Check Digit Verification of cas no

The CAS Registry Mumber 77-06-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 77-06:
(4*7)+(3*7)+(2*0)+(1*6)=55
55 % 10 = 5
So 77-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C19H24O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1

77-06-5 Well-known Company Product Price

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  • Alfa Aesar

  • (45569)  Gibberellic acid, 98%   

  • 77-06-5

  • 0.5g

  • 389.0CNY

  • Detail
  • Alfa Aesar

  • (45569)  Gibberellic acid, 98%   

  • 77-06-5

  • 500mg

  • 408.0CNY

  • Detail
  • Alfa Aesar

  • (45569)  Gibberellic acid, 98%   

  • 77-06-5

  • 2g

  • 531.0CNY

  • Detail
  • Alfa Aesar

  • (45569)  Gibberellic acid, 98%   

  • 77-06-5

  • 10g

  • 2113.0CNY

  • Detail
  • USP

  • (1291005)  Gibberellicacid  United States Pharmacopeia (USP) Reference Standard

  • 77-06-5

  • 1291005-200MG

  • 4,662.45CNY

  • Detail

77-06-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name gibberellin A3

1.2 Other means of identification

Product number -
Other names GIB

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77-06-5 SDS

77-06-5Synthetic route

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

GA3-7-alkohol
54878-53-4

GA3-7-alkohol

B

(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
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
ConditionsYield
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
gibberellin A3-ketone
5087-25-2, 58917-17-2

gibberellin A3-ketone

(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
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
ConditionsYield
With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride
Diacetyl-gibberellinsaeure
19147-54-7, 65563-70-4

Diacetyl-gibberellinsaeure

(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
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
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide at 23℃; for 4h;
gibberellin A5
561-56-8

gibberellin A5

(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
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
ConditionsYield
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;
ent-7α-hydroxykaurene
53060-60-9

ent-7α-hydroxykaurene

(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
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
ConditionsYield
With Giberella fujikuroi at 25℃; for 24h; incubation;
0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd
54878-55-6

0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd

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

B

(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
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
ConditionsYield
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
acetic anhydride
108-24-7

acetic anhydride

(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
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

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

Diacetyl-gibberellinsaeure

Conditions
ConditionsYield
With pyridine; dmap for 12h; Cooling with ice; Inert atmosphere;99%
With pyridine Ambient temperature;2.0 g
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

(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
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

C25H32O6

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

methyl iodide
74-88-4

methyl iodide

gibberellic acid methyl ester
510-50-9

gibberellic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone98%
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 acetone92%
With cesium fluoride In N,N-dimethyl-formamide for 24h; Ambient temperature;407 mg
(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
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

dimethyl sulfate
77-78-1

dimethyl sulfate

gibberellic acid methyl ester
510-50-9

gibberellic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone97%
(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
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

ent-3α,13-dihydroxy-20-norgibberella-1(10),16-diene-7,19-dioic acid
19123-84-3

ent-3α,13-dihydroxy-20-norgibberella-1(10),16-diene-7,19-dioic acid

Conditions
ConditionsYield
With lithium; lithium diisopropyl amide In tetrahydrofuran; ammonia at -78℃;95%
(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
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

C19H24O5
123592-49-4

C19H24O5

Conditions
ConditionsYield
With lithium In ethanol; ammonia at -78℃;93%
N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

(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
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

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-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-carboxylate

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-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-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;93%
benzyl chloride
100-44-7

benzyl chloride

(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
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

C26H28O6
1178-69-4

C26H28O6

Conditions
ConditionsYield
With potassium carbonate In acetone92%
acetic anhydride
108-24-7

acetic anhydride

(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
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

C21H24O7

C21H24O7

Conditions
ConditionsYield
With pyridine; dmap at 20℃;91%
ethyldimethylsilyl chloride
6917-76-6

ethyldimethylsilyl chloride

(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
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

C27H42O6Si2

C27H42O6Si2

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere;89%
(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
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

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

gibberellin A3 3-O-palmitate

gibberellin A3 3-O-palmitate

Conditions
ConditionsYield
With pyridine for 15h; Ambient temperature;83%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

(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
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

C31H50O6Si2

C31H50O6Si2

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere;81%
(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
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

(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
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
ConditionsYield
With hydrogenchloride In water for 3h; Heating;78%
at 250 - 300℃; Product distribution;
(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
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

C19H21IO6
127590-27-6

C19H21IO6

Conditions
ConditionsYield
With Iodine monochloride; sodium hydrogencarbonate In acetonitrile for 5h; Ambient temperature;77%
(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
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

ent-2β,3α,13-trihydroxy-20-norgibberell-1(10),16-diene-7,19-dioic acid 19-2β-lactone

ent-2β,3α,13-trihydroxy-20-norgibberell-1(10),16-diene-7,19-dioic acid 19-2β-lactone

Conditions
ConditionsYield
With water; sodium hydroxide for 1.5h;77%
With tris(pentafluorophenyl)borate; benzo[1,3,2]dioxaborole In dichloromethane at 25℃; for 24h; Reagent/catalyst;
(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
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

(4bS,7S,9aS,10R)-1,7-dimethyl-8-oxo-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
427-78-1

(4bS,7S,9aS,10R)-1,7-dimethyl-8-oxo-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 3h; Wagner-Meerwein Rearrangement;76.5%
With hydrogenchloride
Multi-step reaction with 2 steps
1: aqueous HCl
2: HCl
View Scheme
With hydrogenchloride In water for 2h; Reflux;
(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
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
ConditionsYield
With hydrogenchloride; water at 60℃;75%
With hydrogenchloride at 50℃;
(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
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

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide
14227-90-8

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

gibberellin A3 α-L-(2,3,4,-tri-O-acetyl)arabinopyranosyl ester

gibberellin A3 α-L-(2,3,4,-tri-O-acetyl)arabinopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;75%
(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
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

GA3-7-alkohol
54878-53-4

GA3-7-alkohol

B

C32H44N2O6
58870-20-5

C32H44N2O6

Conditions
ConditionsYield
With sodium tetrahydroborate; dicyclohexyl-carbodiimide In tetrahydrofuran; 1,4-dioxane 1.) -15 deg C, 2.) 5 deg C, 12 h;A 74%
B 3%
(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
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

(S)-oxiranemethanol
60456-23-7

(S)-oxiranemethanol

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-(R)-oxiran-2-ylmethyl 2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9amethanobenzo[a]azulene-10-carboxylate

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-(R)-oxiran-2-ylmethyl 2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9amethanobenzo[a]azulene-10-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;71%
(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
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

C19H24O7
6800-32-4

C19H24O7

Conditions
ConditionsYield
With water; sodium hydroxide for 18h;66%
(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
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

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)glucopyranosyl ester

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)glucopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;63%
2,2,2-trifluorodiazoethane
371-67-5

2,2,2-trifluorodiazoethane

(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
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

acetonitrile
75-05-8

acetonitrile

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-N-acetyl-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-N-(2,2,2-trifluoroethyl)-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxamide

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-N-acetyl-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-N-(2,2,2-trifluoroethyl)-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxamide

Conditions
ConditionsYield
With copper(l) iodide In toluene at 25℃; for 12h;62%
(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
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

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside
3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)galactopyranosyl ester

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)galactopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;61%
(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
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

acetobromocellobiose
14227-66-8

acetobromocellobiose

Gibberellin A3 heptaacetylcellobiosylester
138866-62-3

Gibberellin A3 heptaacetylcellobiosylester

Conditions
ConditionsYield
With triethylamine In acetone for 16h; Ambient temperature;52%
(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
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

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose
3068-31-3

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

gibberellin A3 β-D-(2,3,4,-tri-O-acetyl)xylopyranosyl ester

gibberellin A3 β-D-(2,3,4,-tri-O-acetyl)xylopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;48%
(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
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
ConditionsYield
With hydrogenchloride; water Wagner-Meerwein Rearrangement; Reflux;38%
With hydrogenchloride Heating;
terbium(III) nitrate hexahydrate

terbium(III) nitrate hexahydrate

(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
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

C38H46NO17Tb*4H2O

C38H46NO17Tb*4H2O

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃;35%

77-06-5Relevant articles and documents

PHOTOCYCLISIERUNG EINES GIBBERELLINALDEHYDS ZU EPIMEREN CYCLOBUTANOLEN UND DEREN BASISCHE RUECKSPALTUNG, PARTIALSYNTHESE VON 16,17-DIHYDRO-Δ15-GIBBERELLIN-A3

Lischewski, M.,Adam, G.

, p. 45 - 46 (1980)

UV-irradiation of the aldehyde 1 leads to the 7-epimeric cyclobutanols 2a and 2b which undergo upon treatment with NaOCH3 retroaldol-like cleavage to 1 and 3.Oxidation and deacetylation of 3 affords the 16,17-dihydro-Δ15-gibberellin-A3 (5).

Method of manufacturing a dry water-soluble herbicidal salt composition

-

, (2008/06/13)

A method of manufacturing a solid, water-soluble herbicidal composition comprising a water-soluble salt of a herbicidal compound is disclosed. The herbicidal compound is a water-insoluble compound that includes a carboxylic acid functionality, such as a phenoxy-substituted carboxylic acid compound or a substituted benzoic acid compound, and is sufficiently pure to form a dry, solid herbicidal salt composition after interaction with a suitable neutralizing base, such as ammonia, an alkylamine, a dialkylamine, a trialkylamine, a hydroxyalkylamine, a dihydroxyalkylamine, an alkaline salt of an alkali metal or a combination thereof. The dry herbicidal salt composition includes at least about 90% by weight of the water-soluble herbicidal salt, and dissolves rapidly and essentially completely in water to form an aqueous herbicidal solution including up to about 75% by weight of the water-soluble herbicidal salt.

THE INHIBITION OF GIBBERELLIN PLANT HORMONE BIOSYNTHESIS BY ENT-6-OXO-5&β(H)-7-NORGIBBERELL-16-ENES

Hanson, James R.,Parry, Keith P.,Willis, Christine L.

, p. 1955 - 1958 (2007/10/02)

Ent-19-hydroxy-6-oxo-5β(H)-7-norgibberell-16-ene and the corresponding 19-carboxylic acid are shown to be inhibitors of gibberellin biosynthesis in the fungus, Gibberella fujikuroi, at stages involved in the oxidative modification of ring B of the kaurenoid precursors.Key Word Index - Gibberella fujikuroi; Hypocreales; biosynthesis; gibberellic acid; plant growth regulator.

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