(1R,2R,5R,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid

Base Information

• Chemical Name: (1R,2R,5R,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid
• CAS No.: 77-06-5
• Deprecated CAS: 1405-96-5,192662-67-2,295313-57-4,474760-45-7,58915-44-9,7121-55-3,859282-71-6
• Molecular Formula: C19H22O6
• Molecular Weight: 346.38
• Hs Code.: 29322980
• DSSTox Substance ID: DTXSID0020656
• Mol file: 77-06-5.mol

Synonyms:

Chemical Property of (1R,2R,5R,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 5.93E-18mmHg at 25°C
• Melting Point: 227 °C
• Refractive Index: 81 ° (C=2, MeOH)
• Boiling Point: 628.6 °C at 760 mmHg
• PKA: 4.0(at 25℃)
• Flash Point: 231.4 °C
• PSA: 104.06000
• Density: 1.49 g/cm³
• LogP: 1.02710
• Storage Temp.: 0-6°C
• Solubility.: 5g/l
• Water Solubility.: 5 g/L (20 º C)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 346.14163842
• Heavy Atom Count: 25
• Complexity: 772

Purity/Quality:

90%, ^*data from raw suppliers

Gibberellic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
• Isomeric SMILES: C[C@@]12[C@H](C=C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O
• 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.
• Uses: 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. 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.

Technology Process of (1R,2R,5R,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid

There total 9 articles about (1R,2R,5R,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

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) → GA3-7-alkohol (54878-53-4) + (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)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In tetrahydrofuran; for 0.5h; Yield given;

DOI:10.1016/0040-4020(80)87025-6

Reference yield:

Diacetyl-gibberellinsaeure (19147-54-7,65563-70-4) → (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)

Guidance literature:

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

DOI:10.1016/S0040-4039(00)93620-7

Reference yield:

gibberellin A5 (561-56-8) → (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)

Guidance literature:

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

upstream raw materials:

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

gibberellin A₃-ketone

Diacetyl-gibberellinsaeure

gibberellin A₅

Downstream raw materials:

1,7-Dimethyl-fluoren

C₂₇H₂₈BrIO₈

C₂₆H₂₈O₆

gibberellic acid methyl ester

Refernces

• 1、 -. "Patch preparations for treating plants". . . Retrieved 2008/06/13.
• 2、 Kobayashi, Masatomo,Kwak, Sang-Soo,Kamiya, Yuji,Yamane, Hisakazu,Takahashi, Nobutaka,Sakurai, Akira. "Conversion of GA5 to GA6 and GA3 in Cell-free Systems from Phaseolus vulgaris and Oryza sativa". . p. 249 - 251. Retrieved 2007/10/02.