all pharmacopeias state the tartaric acid in the L(+) isomer only (natural) but not the synthetic racemic form (DL). Since it is used as acidulent and excipient only and no structure- activity relationship is to e expected from the isomer, why the DL form is not stated in the pharmacopeias and has no specification for medical use ? The only difference I could find between them is the optical activity and the higher melting point of the DL form than the L form.
Dear Nashwan,
There is NO scientific reason for not listing the D-(-)-tartaric acid and the meso DL isomers in the pharmacopoeias.
I believe that the natural tartaric acid which is prepared from argols is listed in the pharmacopoeia since it is the naturally occurring isomer and the first to be prepared.
Source and History.—Scheele first prepared this acid in 1769. Retzius, in 1770, produced it in crystalline condition. Tartaric acid is a constituent of grape juice in the form of an acid tartrate of potassium, and is also contained in many other plants, as in the juice of the pineapple, tamarind, sorrel, mulberry, "sumach-bob," etc. The acid of commerce is produced almost exclusively from "crude tartar" or "argols," a refuse by-product in the manufacture of wines. Formerly the American market was chiefly supplied by European manufacturers, but at the present time nearly all of the acid consumed here is produced in the United States from argots shipped from European ports.
Tartaric acid is refrigerant, antiseptic, and antiscorbutic. It is used as a drink in febrile or inflammatory diseases, forming a cooling, refreshing, and agreeable acidulous draught. It is less costly than citric acid, and may be used instead of this acid to form an artificial lemonade. Tartaric acid enters into the composition of Seidlitz, as well as of soda powders. A colorless solution of sulphate of quinine has long been employed by physicians; it may be made by adding equal arts of tartaric acid and sulphate of quinine to as much water as may be desired.
All tartaric acid isomers have the same use and there is no differences excluding their behavior towards polarized light.
http://www.henriettes-herb.com/eclectic/kings/acidum-tart.html
https://en.wikipedia.org/wiki/Tartaric_acid
Hoping this will be helpful,
Rafik
Thank you Dr. Rafik for your reply,
in pharmaceutical manufacture we have to make sure that all the raw materials comply to specifications as stated in the official pharmacopeial monograph before incorporating it in a product ( GMP & local regulations requirement ) In this case we can't do this as the DL is not stated, and when tested according to the monograph, it will fail in the optical rotation and melting point tests !.
I think that the purity of the DL differs also being synthesized in different method than the L isomer. Note that the optical rotation is required by the BP, USP, Japanese pharmacopeias & the Hand book of pharm excipients
When a decision is to be taken, Do you think that the DL consignment should be rejected or used ?
@Michael: Regarding the uses of tartaric acid; there is no scientific studies on the uses that I listed (taken from Henriette's Home Page). Therefore, this information still to be proved.
To my knowledge, tartaric acid is not considered as a medicine; it is a food supplement and is used as a pharmaceutical in the preparation of effervescent tablets.
There is only one official preparation (USP) for tartaric acid:
Related Preparation.—ACIDUM TARTARICUM SACCHARATUM (N. F.), Saccharated tartaric acid. Formulary number, 8: "Tartaric acid (U. S. P.), in very fine powder, six hundred and seventy-five grammes (675 Gm.) [1 lb. av., 7 ozs., 354 grs.]; sugar, in very fine powder, three hundred and twenty-five grammes (325 Gm.) [11 ozs. av., 203 grs.]. Triturate the powders together until intimately mixed, and preserve the product in well-stoppered bottles.
"Note.—This saccharate, when dissolved in water with an equal weight of saccharated sodium bicarbonate (F. 341). will form a neutral solution, and it is introduced into the formulary for the convenient preparation of effervescent powders (F. 319). This saccharate contains 67.5 per cent of tartaric acid"—(.Nat. Form.).
@Nashwan: From my experience as an ex CEO of a pharmaceutical company; for the analysis of any pharmaceutical, you have to use the manufacturer procedure which has to comply with the GMP (FDA) rules. If the analysis of the tartaric acid batch is within the limits put by the manufacturer, this batch can be used.
Rafik
From a pharmaceutical regulatory standpoint, DL is useless! L(+) is the only ingredient permitted! Now from a physical pharmacy viewpoint, if you were using it to make a salt of your API, obviously the properties are going to be different -- there will be crystal differences (esp. if the drug is chiral). Or if you are formulating as a liquid product, this *might* be affected by the solubility difference between the respective (API+acid) solids (if the drug is also chiral).
In vivo (humans), D is more rapidly eliminated than is L, but this is not likely to be a cause for medical concern; also, bacteria, etc. may metabolize the two differently -- only of concern if you're adulterating a wine must, perhaps!
will this be a problem if we use DL tartaric acid instead of L form in home hygiene care products?
Saravanan - That shouldn't be a problem. The acidities are of course equivalent. And you probably have preservatives included, anyway (see comment 2 above).
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