Bacteriochlorophyll a is a naturally occuring photosynthetic pigment isolated from the strain of Chlorobiea and Rhodospirillinea (Rhodopseudomonas sphaeroides).
Physicochemical Properties
| Molecular Formula | C55H74MGN4O6 |
| Molecular Weight | 911.524 |
| Exact Mass | 910.546 |
| Elemental Analysis | C, 72.47; H, 8.18; Mg, 2.67; N, 6.15; O, 10.53 |
| CAS # | 17499-98-8 |
| Related CAS # | 18025-10-0 |
| PubChem CID | 11953947 |
| Appearance | Solid powder |
| Boiling Point | 877.3ºC at 760mmHg |
| Flash Point | 484.4ºC |
| Vapour Pressure | 0mmHg at 25°C |
| LogP | 9.449 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 22 |
| Heavy Atom Count | 66 |
| Complexity | 2100 |
| Defined Atom Stereocenter Count | 7 |
| SMILES | [Mg+2].N1=C2C=C3[N-]C(C(=C3C)C(=O)C)=CC3=NC(=CC4=C(C5C(=O)C(C(=O)OC)C(=C1C(CCC(OC/C=C(/CCCC(CCCC(CCCC(C)C)C)C)\C)=O)C2C)C=5[N-]4)C)C(C3C)CC |c:2,12,16,t:28| |
| InChi Key | DSJXIQQMORJERS-AGGZHOMASA-M |
| InChi Code | InChI=1S/C55H75N4O6.Mg/c1-13-39-34(7)41-29-46-48(38(11)60)36(9)43(57-46)27-42-35(8)40(52(58-42)50-51(55(63)64-12)54(62)49-37(10)44(59-53(49)50)28-45(39)56-41)23-24-47(61)65-26-25-33(6)22-16-21-32(5)20-15-19-31(4)18-14-17-30(2)3/h25,27-32,34-35,39-40,51H,13-24,26H2,1-12H3,(H-,56,57,58,59,60,62)/q-1+2/p-1/b33-25+/t31-,32-,34-,35+,39-,40+,51-/m1./s1 |
| Chemical Name | magnesiummethyl (3R,11R,12R,21S,22S)-16-acetyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-[3-oxo-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-23,25-diaza-7,24-diazanidahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1(23),2(6),5(26),8,10(25),13,15,17,19-nonaene-3-carboxylate |
| Synonyms | C11242C-11242Bacteriochlorophyll a Bacteriochlorophyll Bacteriochlorophyll from Rhodopseudomonas sphaeroides |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | The bacteriochlorophyll (BChl) a protein from Chlorobium tepidum, which participates in energy transfer in green photosynthetic bacteria, has been crystallized using the sitting drop method of vapor diffusion. X-ray diffraction data collected from these crystals indicate that the crystals belong to the cubic space group P4132 with cell dimensions of a=b=c=169.5 A. A native X-ray diffraction data set has been collected to a resolution of 2.2 A. The initial solution was determined by using the molecular replacement method using the structure of the previously solved BChl a protein from Prosthecochloris aestuarii. A unique rotation and translation solution was obtained for two monomers in the asymmetric unit giving a pseudo-body centered packing. After rebuilding and refinement the model yields an R factor of 19.0%, a free R-factor of 28.3%, and good geometry with root-mean-square deviations of 0.013 A and 2.1 degrees for the bond lengths and angles, respectively. The structure of the BChl a protein from C. tepidum consists of three identical subunits related by a 3-fold axis of crystallographic symmetry. In each subunit the polypeptide backbone forms large beta-sheets and encloses a central core of seven BChl a molecules. The distances between neighboring bacteriochlorin systems within a subunit range between 4 A to 11 A and that between two bacteriochlorins from different subunits is more than 20 A. The overall structure is comparable with that of P. aestuarii but significant differences are observed for the individual bacteriochlorophyll structures. The surface of the trimer has a hydrophobic region that is modeled as the complex being a peripheral membrane protein partially embedded in the membrane. A general model is presented for the membrane organization with two of the bacteriochlorophyll structures in the membrane and transferring energy to the reaction center complex. In this model these two bacteriochlorophyll structures serve a similar role to the cofactors of integral membrane light-harvesting complexes although the protein structure surrounding the cofactors is significantly different for the BChl a protein compared with the integral membrane complexes.[1] |
| References |
[1]. Crystal structure of the bacteriochlorophyll a protein from Chlorobium tepidum. Journal of molecular biology 271.3 (1997): 456-471. |
| Additional Infomation |
A specific bacteriochlorophyll that is similar in structure to CHLOROPHYLL A. Pyrrole containing pigments found in photosynthetic bacteria. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0971 mL | 5.4853 mL | 10.9707 mL | |
| 5 mM | 0.2194 mL | 1.0971 mL | 2.1941 mL | |
| 10 mM | 0.1097 mL | 0.5485 mL | 1.0971 mL |